Butyric Acid → Ethyl 4-[(3-methoxyphenyl)sulfanyl]-3-oxobutanoate

HRID 2261832Notes

Reaction equation

HRID 2261832 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-:11].[K+].[K+].[C:16]([OH:21])(=[O:20])[CH2:17][CH2:18][CH3:19].[C:22](#N)[CH3:23]>>[CH2:22]([O:20][C:16](=[O:21])[CH2:17][C:18](=[O:11])[CH2:19][S:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:23]

Participants

5

Reactant 4

HCID 264Butyric AcidHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 849893-Methoxybenzenethiol

Product 1

HCID 21816283Ethyl 4-[(3-methoxyphenyl)sulfanyl]-3-oxobutanoateYield 99%

Procedure

To a solution of 3-methoxy-benzenethiol (5.75 g, 41.0 mmol) and potassium carbonate (11.45 g, 82.02 mmol) in acetonitrile (150 mL) is added butanoic acid, 4-chloro-3-oxo-, ethyl ester (6.12 mL, 45.11 mmol) at 0° C. The mixture is stirred at room temperature for 2 hours and filtered through a pad of Celite®. The filtrate is concentrated and purified by silica gel chromatography with 25-30% EtOAc/Hexanes to provide 4-(3-methoxy-phenylsulfanyl)-3-oxo-butyric acid ethyl ester (10.9 g, 99%) ES/MS m/e 267.0 (M−1).

Workup

  1. filtrationfiltered through a pad of Celite®
  2. concentrationThe filtrate is concentrated
  3. custompurified by silica gel chromatography with 25-30% EtOAc/Hexanes

Sources & evidence

ORD record
ord-877d8aa7d452426894fc85c12e0a1f63
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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