Reaxys
PubChem
eMolecules
Reactions (9)
Yield
Substances (4)
Citations (12)
Conditions
References
1
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With potassium permanganate in tetrahydrofuran; water; ethyl acetate
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Rx-ID: 24503118 Find similar reactions
Zeneca Limited
Patent: US5393877 A1, 1995 ; Title/Abstract Full Text Show Details
5.1.a:a)
a) Preparation of r-3,Cis-4-dihydroxy-cis plus trans-2,-trans-5-dimethoxytetrahydrofuran STR29 2,5-Dihydro-2,5-dimethoxyfuran (50 g; Aldrich, cis/trans mixture) was dissolved in tetrahydrofuran (500 ml) in a 5 liter, three-necked flask fitted with a mechanical stirrer. The contents of the flask were cooled to -5° C., and a solution of potassium permanganate (61.9 g) in water (2250 ml) was added dropwise with vigorous stirring at such a rate as to keep the temperature of the flask contents between 4° and 6° C. This addition took 80 minutes. The reaction mixture was then left stirring and allowed to warm to room temperature over 15 hours. The precipitated manganese dioxide was filtered off through Celite and washed with THF (200 ml). The clear colourless filtrate was evaporated and the residue was shaken vigorously with ethyl acetate (200 ml) until no material adhered to the flask wall. The fine precipitate of KOH was filtered off on a glass sinter and washed with ethyl acetate. The filtrate was rotary evaporated to give the title compound as a golden syrup (24.4 g, 38.6percent). The compound was mainly the meso product (80percent) contaminated with the dl compound (20percent).
2
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Rx-ID: 1589488 Find similar reactions
56%
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With hydrogenchloride
T=-70 - -65°C;
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Hirai, Kenji; Suzuki, Hiroharu; Moro-oka, Yoshihiko; Ikawa, Tsuneo
Tetrahedron Letters, 1980 , vol. 21, p. 3413 - 3416 Title/Abstract Full Text View citing articles Show Details
A
B
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3
Synthesize Find similar Rx-ID: 76015 Find similar reactions
With methanol; nickel; sodium carbonate
Hydrogenation;
Imp. Chem. Ind.
Patent: US2465988 , 1947 ; Full Text Show Details
Imp. Chem. Ind.
Patent: DE972256 , 1951 ; DRP/DRBP Org.Chem. Full Text Show Details
Clauson-Kaas et al.
Acta Chemica Scandinavica (1947-1973), 1950 , vol. 4, p. 1233,1239 Full Text View citing articles Show Details
Basilewskaja et al.
Zhurnal Obshchei Khimii, 1958 , vol. 28, p. 1097,1099; engl. Ausg. S. 1065, 1067 Full Text Show Details
With methanol; nickel kieselguhr-catalyst
P=22065.2 - 36775.4 Torr; Hydrogenation;
Imp. Chem. Ind.
Patent: US2465988 , 1947 ; Full Text Show Details
Imp. Chem. Ind.
Patent: DE972256 , 1951 ; DRP/DRBP Org.Chem. Full Text Show Details
Clauson-Kaas et al.
Acta Chemica Scandinavica (1947-1973), 1950 , vol. 4, p. 1233,1239 Full Text View citing articles Show Details
Basilewskaja et al.
Zhurnal Obshchei Khimii, 1958 , vol. 28, p. 1097,1099; engl. Ausg. S. 1065, 1067 Full Text Show Details
4
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Rx-ID: 806737 Find similar reactions
With methanol; nickel
P=73550.8 Torr; Hydrogenation;
Nielsen et al.
Acta Chemica Scandinavica (1947-1973), 1958 , vol. 12, p. 63,65 Full Text View citing articles Show Details
Gagnaire; Vottero
Bulletin de la Societe Chimique de France, 1970 , p. 164,166 Full Text View citing articles Show Details
5
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With methanol; nickel
P=73550.8 Torr; Hydrogenation;
Rx-ID: 806739 Find similar reactions
Nielsen et al.
Acta Chemica Scandinavica (1947-1973), 1958 , vol. 12, p. 63,65 Full Text View citing articles Show Details
Gagnaire; Vottero
Bulletin de la Societe Chimique de France, 1970 , p. 164,166 Full Text View citing articles Show Details
A
B
C
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6
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Rx-ID: 2892043 Find similar reactions
With 2,3-dimercapto-succinic acid; ozone
1) -78 deg C; Yield given. Multistep reaction. Yields of byproduct given;
Griesbaum, Karl; Jung, In Chang; Mertens, Henri
Journal of Organic Chemistry, 1990 , vol. 55, # 24 p. 6024 - 6027 Title/Abstract Full Text View citing articles Show Details
7
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Rx-ID: 24547943 Find similar reactions
Sankyo Company, Limited
Patent: US5472972 A1, 1995 ;
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Title/Abstract Full Text Show Details
...compounds: such as 10,10'-oxybis-10H-phenoxarsine; other antimicrobial agents, including other fungicides and anthelmintics: such as 2-(4-thiazolyl)-1H-benzimidazole, N-(dichlorofluoromethylthio)phthalimide and N,N-dimethyl-N'-(dichlorofluoromethylthio)sulfamide. Of these, we prefer: 1,5-pentanedial (hereinafter referred to as Compound B-1), 2,5-dimethoxytetrahydrofuran (hereinafter referred to as Compound B-2), glyoxal (hereinafter referred to as Compound B-3), benzalkonium chloride (hereinafter referred to as Compound B-4), 1,2-benzisothiazolin-3-one (hereinafter referred to as Compound B-5), cupric hydroxide (hereinafter referred to as Compound B-6), 4-chloro-2-xylenol (hereinafter referred to as Compound B-7), 4-chloro-2-cresole (hereinafter referred to as Compound B-8), ...
8
Synthesize Find similar Trennung von Verb. Nr. 17-0039727-02;
Rx-ID: 5703733 Find similar reactions
Nielsen et al.
Acta Chemica Scandinavica (1947-1973), 1958 , vol. 12, p. 63,65 Full Text View citing articles Show Details
Kankaanpera; Miiki
Acta Chemica Scandinavica (1947-1973), 1969 , vol. 23, p. 1471,1472,1473 Full Text Show Details
Aito et al.
Bulletin of the Chemical Society of Japan, 1967 , vol. 40, p. 130,131,132 Full Text Show Details
9
Synthesize Find similar Trennung von Verb. Nr. 17-003927-01;
Rx-ID: 5703734 Find similar reactions
Nielsen et al.
Acta Chemica Scandinavica (1947-1973), 1958 , vol. 12, p. 63,65 Full Text View citing articles Show Details
Kankaanpera; Miiki
Acta Chemica Scandinavica (1947-1973), 1969 , vol. 23, p. 1471,1472,1473 Full Text Show Details
Aito et al.
Bulletin of the Chemical Society of Japan, 1967 , vol. 40, p. 130,131,132 Full Text Show Details