HCID 59750856, compound → 4-Methanesulfonylbutan-1-ol
Reaction equation
C([Si]([O:18][CH2:19][C:20]1C=CC=C[C:21]=1[CH2:26][S:27]([C:30]1C=CC(Cl)=CC=1)(=[O:29])=[O:28])(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C>C1(C)C=CC=CC=1>[CH3:30][S:27]([CH2:26][CH2:21][CH2:20][CH2:19][OH:18])(=[O:29])=[O:28]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
In toluene (5 ml) were dissolved t-butyl [[2-[[(4-chlorophenyl)sulfonyl]methyl]benzyl]oxy]diphenylsilane (350 mg, 0.654 mmol) and the 4-(methylsulfonyl)-1-butanol (200 mg, 1.31 mmol) obtained in Referential Example 3, followed by the addition of cyanomethylenetri-n-butylphosphorane (350 mg, 1.45 mmol). Under an argon atmosphere, the resulting mixture was heated under reflux for 14 hours. After the reaction mixture was allowed to cool down, cyanomethylenetri-n-butylphosphorane (300 mg, 1.24 mmol) was added thereto. Under an argon atmosphere, the resulting mixture was heated under reflux for 14 hours. The reaction mixture was then allowed to cool down. The residue obtained by concentrating the mixture under reduced pressure was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=3:2 was concentrated under reduced pressure, whereby the title compound (175 mg, 0.261 mmol, 40%) was obtained as a pale yellowish brown oil.
Sources & evidence
- ORD record
- ord-cf077adff605400b8c4faec03ff0a389
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07399775B2
Reaction notes
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