Ethyl 4-[(3-methoxyphenyl)sulfanyl]-3-oxobutanoate → 4-Methoxy-benzo[b]thiophen-3-yl-acetic acid ethyl ester

HRID 490688Notes

Reaction equation

HRID 490688 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6](=O)[CH2:7][S:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)[CH3:2]>CS(O)(=O)=O>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6]1[C:14]2[CH:13]=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=2[S:8][CH:7]=1)[CH3:2].[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6]1[C:10]2[C:11]([O:15][CH3:16])=[CH:12][CH:13]=[CH:14][C:9]=2[S:8][CH:7]=1)[CH3:2]

Participants

4

Reactant 1

HCID 21816283Ethyl 4-[(3-methoxyphenyl)sulfanyl]-3-oxobutanoate

Product 2

HCID 218162724-Methoxy-benzo[b]thiophen-3-yl-acetic acid ethyl esterHCID 21816275Ethyl 2-(6-methoxybenzo[b]thiophen-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

4-(3-Methoxy-phenylsulfanyl)-3-oxo-butyric acid ethyl ester (10.0 g) is added to pre-cooled methanesulfonic acid (60 mL) at 0˜5° C., then the reaction mixture is allowed to warm to room temperature. After 1 h, the mixture is diluted with ice water and extracted with ethyl acetate. The combined organics are washed with brine, dried over Na2SO4, concentrated. Chromatography on silica gel elited with hexanes and ethyl acetate yields (6-methoxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester (4.8 g) and (4-methoxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester (0.8 g)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organics are washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-376bf15725554d6d8b93e98293dc63db
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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