Query Query O
1. Query
ARY
ARY
Results
Date
10 reactions in Reaxys
2017-11-15 03h:11m:04s (EST)
Search as: As drawn, No salts, No mixtures
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
1/5
2017-11-15 03:11:26
O OH
HO OH
OH
Rx-ID: 32433317 View in Reaxys 1/10 Yield
Conditions & References
91 %
27. 5-Propyl-3'-prop-2-ynyl-biphenyl-2,4'-diol (29) To a solution of 28 (200 mg, 0.48 mmol) in dioxane-H2O (1:1, 15 mL) was added an NaOH solution (20percent in water) and the mixture was heated at 60 °C for 2 h at which time TLC indicated total disappearance of starting material. Then it was cooled to room temperature and was adjusted the pH to 5-6 by drop wise addition of 1 M HCl solution. The resultant white turbidity was taken up in dichloromethane (15 mL) and washed with brine (2 .x.10 mL) followed by drying and concentration to afford a residue (180 mg, 0.46 mmol, 96percent). The residue was dissolved in MeOH (15 mL) and resulting solution was cooled in a ice bath. To this solution a saturated aqueous solution of NaIO4 (144 mg, 0.67 mmol) was drop wisely added resulting in a white turbidity. The cold solution was stirred for 45 min at which time all the starting material disappeared. The mixture was filtered over celite to get rid of all of solid materials and the solvent was evaporated to give a residue which was extracted with EtOAc (15 mL). The extract was washed with brine and concentrated under reduced pressure to furnish a thick gummy residue (140 mg, 0.39 mmol, 85percent). The vacuum dried residue (108 mg, 0.30 mmol) solution in dichloromethane (2 mL) was slowly added to a cold orange suspension mixture of CBr4 (299 mg, 0.9 mmol), PPh3 (471 mg, 1.8 mmol) and K2CO3 (248 mg, 1.8 mmol) in dichloromethane (5 mL) under argon at 10 °C. The mixture was stirred for further 15 min at the same temperature at which time all the starting material was consumed. It was diluted with dichloromethane (15 mL) and passed through a short pad of silica gel to get rid of the triphenylphosphine oxide as far as possible, followed by concentration to afford a yellow oil (140 mg, 0.27 mmol, 91 percent). With carbon tetrabromide, potassium carbonate, triphenylphosphine in dichloromethane, Time= 0.25h, T= 10 °C , Inert atmosphere Tripathi, Subhankar; Chan, Ming-Huan; Chen, Chinpiao; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 1; (2012); p. 216 - 221 View in Reaxys
O S
O
O
O
O
S
O
O
O
O
Rx-ID: 32433009 View in Reaxys 2/10 Yield 155 mg
Conditions & References 4. 5'-Allyl-2'-methoxy-biphenyl-4-ol (6) General Procedure: To a solution of compound 5 (3.24 g, 9.1 mmol) in dry DCM (50 mL) was added TEA (4.5 mL, 32.3 mmol) under argon atmosphere and the resultant mixture was cooled in an ice-bath for 30 min. To this cold solution methanesulfonyl chloride (2.13 mL, 27.5 mmol) was added slowly over a period of 5 min. The mixture was stirred at room temperature for 2 h at which time TLC revealed complete conversion. More DCM (50 mL) was added and the organic phase was repeatedly washed with saturated NaHCO3 solution (2 20 mL) and brine (3 20 mL). The organic phase was dried over MgSO4 and concentrated under vacuo to afford the crude product (5.7 g) which was dissolved in dry DMF (50 mL) followed by addition of NaI (5.48 g, 36.8 mmol) and zinc dust (8.84 g, 138.2 mmol) under argon atmosphere. The mixture was heated at 140 °C for 18 h when TLC showed complete conversion. The DMF solution was filtered through celite to remove all the solid materials and washed with EtOAc followed by concentration under vacuum to remove DMF as far as possible. The residue is then poured into water and extracted with EtOAc (2 50 mL). The organic layer was washed with brine (3 30 mL) and dried over MgSO 4 followed by concentration under vacuum to furnish the crude product. Purification on a silica gel column using a mixture of EtOAchexanes (3:22) afforded 6 (1.84 g, 7.7 mmol, 85percent for two steps) as a colourless oil.
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
2/5
2017-11-15 03:11:26
With sodium iodide, zinc in N,N-dimethyl-formamide, Time= 18h, T= 140 °C , Inert atmosphere Tripathi, Subhankar; Chan, Ming-Huan; Chen, Chinpiao; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 1; (2012); p. 216 - 221 View in Reaxys
2
H
O
2
I
Br
2
H
H 2
H
I
Br
Rx-ID: 29372487 View in Reaxys 3/10 Yield
Conditions & References
48 %
Stage 1: With chloro-trimethyl-silane, titanium tetrachloride, ethylene dibromide, zinc in tetrahydrofuran, Time= 0.5h, T= 20 °C , Inert atmosphere Stage 2: in tetrahydrofuran, Time= 0.5h, T= 20 °C , Inert atmosphere Stage 3: With hydrogenchloride, water in tetrahydrofuran Schultz, Danielle M.; Wolfe, John P.; Organic Letters; vol. 12; nb. 5; (2010); p. 1028 - 1031 View in Reaxys
O Si 2
O
O
H
E
Si
Rx-ID: 41120644 View in Reaxys 4/10 Yield
Conditions & References Reaction Steps: 3 1.1: triphenylphosphine / dichloromethane / 0.67 h / 0 °C / |Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - 20 °C / |Inert atmosphere 3.1: Schwartz's reagent / tetrahydrofuran / 2.5 h / |Inert atmosphere 3.2: 18 h / 20 °C / |Inert atmosphere With Schwartz's reagent, n-butyllithium, triphenylphosphine in tetrahydrofuran, hexane, dichloromethane White, Derick R.; Hutt, Johnathon T.; Wolfe, John P.; Journal of the American Chemical Society; vol. 137; nb. 35; (2015); p. 11246 - 11249 View in Reaxys O 2
OH
H
E
O Si
Rx-ID: 41120645 View in Reaxys 5/10 Yield
Conditions & References Reaction Steps: 4 1.1: triphenylphosphine / dichloromethane / 0.67 h / 0 °C / |Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - 20 °C / |Inert atmosphere 3.1: Schwartz's reagent / tetrahydrofuran / 2.5 h / |Inert atmosphere 3.2: 18 h / 20 °C / |Inert atmosphere 4.1: tetrabutyl ammonium fluoride / dichloromethane; tetrahydrofuran / 1.5 h / 20 °C / |Inert atmosphere With Schwartz's reagent, n-butyllithium, tetrabutyl ammonium fluoride, triphenylphosphine in tetrahydrofuran, hexane, dichloromethane White, Derick R.; Hutt, Johnathon T.; Wolfe, John P.; Journal of the American Chemical Society; vol. 137; nb. 35; (2015); p. 11246 - 11249 View in Reaxys
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
3/5
2017-11-15 03:11:26
O
Cl Cl
Cl Ge
Ti
(v4)
Rx-ID: 2393358 View in Reaxys 6/10 Yield
Conditions & References
82 %
in diethyl ether, Time= 15h, from 0 degC to 20 degC Kauffmann, Thomas; Koenig, Rolf; Pahde, Claudia; Tannert, Annegret; Tetrahedron Letters; vol. 22; nb. 50; (1981); p. 5031 - 5034 View in Reaxys 2
2H
2H
I
2
H
O
2
H
H
Rx-ID: 33804027 View in Reaxys 7/10 Yield
Conditions & References With C44H58Cl2N4Pd in methanol, Wittig reaction Spallek, Markus J.; Stockinger, Skrollan; Goddard, Richard; Trapp, Oliver; Advanced Synthesis and Catalysis; vol. 354; nb. 8; (2012); p. 1466 - 1480 View in Reaxys O
O
O O
O
O HO
Rx-ID: 13707671 View in Reaxys 8/10 Yield
Conditions & References Reaction Steps: 2 1.1: tBuOK; 18-crown-6 / tetrahydrofuran / 0.5 h / -78 °C 1.2: 50 percent / tetrahydrofuran / -78 °C 2.1: 85 percent / LiOH*H2O; H2O / methanol / 48 h / 70 °C With lithium hydroxide, 18-crown-6 ether, potassium tert-butylate, water in tetrahydrofuran, methanol, 1.2: Wittig reaction Yadav; Srihari; Tetrahedron Asymmetry; vol. 15; nb. 1; (2004); p. 81 - 89 View in Reaxys
O S
O
O
OH
O
O O
S
O
O
Rx-ID: 32433010 View in Reaxys 9/10 Yield
Conditions & References Reaction Steps: 2 1: sodium iodide; zinc / N,N-dimethyl-formamide / 18 h / 140 °C / Inert atmosphere 2: diethylaluminium chloride / hexane; dichloromethane / 2 h / 20 °C With diethylaluminium chloride, sodium iodide, zinc in hexane, dichloromethane, N,N-dimethyl-formamide, 2: Claisen rearrangement Tripathi, Subhankar; Chan, Ming-Huan; Chen, Chinpiao; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 1; (2012); p. 216 - 221
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
4/5
2017-11-15 03:11:26
View in Reaxys O S
O
O
O
OH
O
HO
Rx-ID: 32433011 View in Reaxys 10/10 Yield
Conditions & References Reaction Steps: 3 1: sodium iodide; zinc / N,N-dimethyl-formamide / 18 h / 140 °C / Inert atmosphere 2: diethylaluminium chloride / hexane; dichloromethane / 2 h / 20 °C 3: sodium hydroxide / 1,4-dioxane; water / 2 h / 60 °C With diethylaluminium chloride, sodium iodide, sodium hydroxide, zinc in 1,4-dioxane, hexane, dichloromethane, water, N,N-dimethyl-formamide, 2: Claisen rearrangement Tripathi, Subhankar; Chan, Ming-Huan; Chen, Chinpiao; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 1; (2012); p. 216 - 221 View in Reaxys
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
5/5
2017-11-15 03:11:26