Water → Methyl [(2-oxobutyl)sulfanyl]acetate

HRID 1061664Notes

Reaction equation

HRID 1061664 reaction equation
C(N(CC)CC)C.[OH:8][CH:9]([CH2:17][CH3:18])[CH2:10][S:11][CH2:12][C:13]([O:15][CH3:16])=[O:14].O>CS(C)=O>[O:8]=[C:9]([CH2:17][CH3:18])[CH2:10][S:11][CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 22284251Methyl 2-(2-hydroxybutylthio)acetate

Product 1

HCID 12353742Methyl [(2-oxobutyl)sulfanyl]acetate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Triethylamine (28.3 ml) is added to a solution of methyl 2-(2-hydroxybutylthio)acetate (6.00 g, Reference compound No. 35-1) in dimethyl sulfoxide (180 ml). A sulfur trioxide-pyridine complex (20.0 g) is added to the mixture, and the whole is stirred for one hour. Water is added to the reaction mixture, and the whole is stirred for 20 minutes and extracted with ethyl acetate. The extract is washed with water, 1 N hydrochloric acid and saturated brine successively and dried over anhydrous magnesium sulfate. The extract is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give the titled reference compound (5.93 g).

Workup

  1. additionA sulfur trioxide-pyridine complex (20.0 g) is added to the mixture
  2. stirringthe whole is stirred for 20 minutes
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with water, 1 N hydrochloric acid and saturated brine successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe extract is concentrated under reduced pressure
  7. customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-041cbb27fc20401c92b6a987c39cc489
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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