Methanesulfonic Acid → 4-Methoxy-benzo[b]thiophen-3-yl-acetic acid ethyl ester

HRID 250262Notes

Reaction equation

HRID 250262 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: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

3

Reactant 2

HCID 6395Methanesulfonic AcidHCID 21816283Ethyl 4-[(3-methoxyphenyl)sulfanyl]-3-oxobutanoate

Product 1

HCID 218162724-Methoxy-benzo[b]thiophen-3-yl-acetic acid ethyl esterYield 59%

Procedure

4-(3-methoxy-phenylsulfanyl)-3-oxo-butyric acid ethyl ester (10.9 g, 40.62 mmol) is added to methanesulfonic acid (26.6 mL, 406 mmol). The mixture is stirred at room temperature for 30 minutes. The reaction mixture is poured into ice-water (300 g) and extracted with EtOAc (100 mL×2). The combined organic layers are dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product is purified by flash chromatography eluting with 20% EtOAc/Hexanes. The appropriate fractions are combined and concentrated under reduced pressure to afford the title compound (6.00 g, 59%). ES/MS n/e 251.0 (M+1)

Workup

  1. extractionextracted with EtOAc (100 mL×2)
  2. dry with materialThe combined organic layers are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product is purified by flash chromatography
  6. washeluting with 20% EtOAc/Hexanes
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a18fbf41db104f23a8d6e5401c2f5d4d
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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