Acetone → (E)-3-Cyclopentyl-2-(4-methanesulfonyl-phenyl)-acrylic acid ethyl ester

HRID 2103607Notes

Reaction equation

HRID 2103607 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[CH2:7]([O:9][C:10](=[O:26])/[C:11](/[C:18]1[CH:23]=[CH:22][C:21](SC)=[CH:20][CH:19]=1)=[CH:12]/[CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH3:8].[CH3:27]C(C)=O>O>[CH2:7]([O:9][C:10](=[O:26])/[C:11](/[C:18]1[CH:23]=[CH:22][C:21]([S:3]([CH3:27])(=[O:5])=[O:2])=[CH:20][CH:19]=1)=[CH:12]/[CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH3:8]

Participants

5

Reactant 3

HCID 180AcetoneHCID 23707502Potassium hydroxy sulfiteHCID 67084466(E)-3-Cyclopentyl-2-(4-methylsulfanyl-phenyl)-acrylic acid ethyl ester

Product 1

HCID 67084405(E)-3-Cyclopentyl-2-(4-methanesulfonyl-phenyl)-acrylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Add a suspension of oxone® (113 g, 183 mmol) in water (600 ml) to a solution of (E)-3-cyclopentyl-2-(4-methylsulfanyl-phenyl)-acrylic acid ethyl ester (24.2 g, 83 mmol) in acetone (600 ml). Stir overnight, and then add water (500 ml). Extract the resulting mixture with dichloromethane (2×500 ml). Combine the extracts, wash with brine (2×500 ml), dry over magnesium sulfate, and remove solvent under vacuum to afford the title compound as an off-white solid (25.8 g). MS (m/e): 323.4 (M+H).

Workup

  1. additionAdd
  2. extractionExtract the resulting mixture with dichloromethane (2×500 ml)
  3. washCombine the extracts, wash with brine (2×500 ml)
  4. dry with materialdry over magnesium sulfate
  5. customremove solvent under vacuum

Sources & evidence

ORD record
ord-18143582233242d89b76583e80b57302
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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