Query Query
Results
Date
1 reactions in Reaxys
2017-12-21 22h:10m:49s (EST)
O
1. Query
O O SH
Search as: As drawn
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.
1/2
2017-12-21 22:14:46
O
H N
O
O
O
O
O Br
O SH
Rx-ID: 25455566 View in Reaxys 1/1 Yield 56%
Conditions & References 32.A : Example 32 A. 3-(2,2-diethoxyethylthio)-4,5-diemethoxybenzaldehyde Morpholine (2.61g, 0.03 mol) and 50 ml of dry tetrahydrofuran were placed in a flame-dried three neck flask under nitrogen, and chilled to -70°C. Then n-butyl lithium (20.6 ml, 0.033 mol, 1.6 M in hexane) was added dropwise via an addition funnel, keeping the temperature at -70°. Then 5-bromo-3,4-dimethoxy-benzaldehyde (0.03 mol) dissolved in 25 ml of tetrahydrofuran was added slowly, and then the reaction was stirred for 1 hour at -50°. A second equivalent of n-butyl lithium (20.6 ml, 0.033 mol) was then added, followed by sulfur (1.06g, 0.033 mol) via a Gooch tube, and the reaction was stirred for 1 hour. Then the reaction was poured onto cold water, acidified to pH 5 with 1 N hydrochloric acid, and extracted with ethyl acetate and evaporated to give 3.35g (56percent yield) of crude 3,4-dimethoxy-5-mercaptobenzaldehyde. The crude mercaptobenzaldehyde from above (2.78g, 14 mmol) was slurried in 1.25 ml of absolute ethanol under nitrogen. With n-butyllithium, hydrogen sulfide in tetrahydrofuran, hexane Patent; THE WELLCOME FOUNDATION LIMITED; EP96214; (1991); (B1) English 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.
2/2
2017-12-21 22:14:46