Methyl Thioglycolate → Methyl 4-[(2-methoxy-2-oxoethyl)sulfanyl]butanoate

HRID 2299101Notes

Reaction equation

HRID 2299101 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].C[O-].[Na+].Br[CH:11]([CH2:16][CH3:17])[C:12]([O:14][CH3:15])=[O:13]>CO>[CH3:6][O:5][C:1](=[O:4])[CH2:2][S:3][CH2:17][CH2:16][CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 95577Butanoic acid, 2-bromo-, methyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 18379236Methyl 4-[(2-methoxy-2-oxoethyl)sulfanyl]butanoateYield 55.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl thioglycolate (5.0 mL, 55.0 mmol) was added dropwise to an ice cold solution of sodium methoxide (55.0 mmol) in methanol (18 mL) over 15 minutes. Methyl bromobutyrate (9.9 g, 55.0 mmol) was added slowly. The reaction was allowed to warm to room temperature and stirred overnight. The resulting mixture was filtered, concentrated, and taken up in methylene chloride and filtered again. The filtrate was concentrated and the product was distilled to give methyl 4-[(2-methoxy-2-oxoethyl)sulfanyl]butanoate (6.34 g, 55%) as a clear oil.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationconcentrated
  3. filtrationfiltered again
  4. concentrationThe filtrate was concentrated
  5. distillationthe product was distilled

Sources & evidence

ORD record
ord-2bda57633d80439f845cfe1de5759a30
Source dataset
uspto-grants-2002_12
Patent number
US06495565B2

Reaction notes

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