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

HRID 250261Notes

Reaction equation

HRID 250261 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-].[K+].[K+].C(O)(=O)CCC.[CH2:22]([O:24][C:25](=[O:31])[CH2:26][C:27](=[O:30])[CH2:28]Cl)[CH3:23]>C(#N)C>[CH2:22]([O:24][C:25](=[O:31])[CH2:26][C:27](=[O:30])[CH2:28][S:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:23]

Participants

6

Reactant 4

HCID 264Butyric AcidHCID 11430Potassium CarbonateHCID 69484Ethyl 4-chloroacetoacetateHCID 849893-Methoxybenzenethiol

Product 1

HCID 21816283Ethyl 4-[(3-methoxyphenyl)sulfanyl]-3-oxobutanoateYield 99.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 0° C. 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-butanoic acid ethyl ester 6.12 mL, 45.11 mmol). The mixture is stirred at room temperature for 2 hours and filtered through a pad of diatomaceous earth. The filtrate is concentrated under reduced pressure. The residue is purified via silica gel chromatography eluting with 25-30% EtOAc/Hexanes to provide the title compound (10.9 g, 99%). MS: 267.0 (M−1)

Workup

  1. filtrationfiltered through a pad of diatomaceous earth
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customThe residue is purified via silica gel chromatography
  4. washeluting with 25-30% EtOAc/Hexanes

Sources & evidence

ORD record
ord-c62ece3bbcde4a36a9634fb8e248ee88
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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