p-Chlorothiophenol → 2-(4-chlorophenylsulfanyl)-3-oxobutyric Acid Methyl Ester

HRID 2266471Notes

Reaction equation

HRID 2266471 reaction equation
[CH3:1][O:2][C:3](=[O:9])[CH:4](Cl)[C:5](=[O:7])[CH3:6].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([SH:17])=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3](=[O:9])[CH:4]([S:17][C:14]1[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][CH:13]=1)[C:5](=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 8471TriethylamineHCID 107332Methyl 2-chloroacetoacetate

Product 1

HCID 125614692-(4-chlorophenylsulfanyl)-3-oxobutyric Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-3-oxobutyric acid methyl ester (3.5 g) and 4-chlorobenzenethiol (4.1 g) in dichloromethane (60 mL) at 0° C. was added triethylamine (4.0 mL). The mixture was warmed to room temperature and then stirred at this temperature for 3 days. The solvent was removed under reduced pressure and the residue diluted with ethyl acetate and this mixture was washed with saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and cyclohexane (1:4 by volume) to afford title compound as a waxy solid, 7.2 g.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue diluted with ethyl acetate
  3. washthis mixture was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue purified by column chromatography on silica gel
  7. washeluting with a mixture of ethyl acetate and cyclohexane (1:4 by volume)

Sources & evidence

ORD record
ord-2792f07a008549a199b6d359e3d9a840
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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