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HCID 59750856, compound → 4-Methanesulfonylbutan-1-ol

HRID 748817
Notes
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Reaction equation

HRID 748817 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]
ParticipantsProcedureSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 59750856HCID 59750856, compound

Product 1

HCID 230286054-Methanesulfonylbutan-1-olYield 200.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07399775B2

Reaction notes

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