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

HRID 2103651Notes

Reaction equation

HRID 2103651 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[CH2:7]([O:9][C:10](=[O:27])/[C:11](/[C:19]1[CH:24]=[CH:23][C:22](SC)=[CH:21][CH:20]=1)=[CH:12]/[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH3:8].[CH3:28]C(C)=O>O>[CH2:7]([O:9][C:10](=[O:27])/[C:11](/[C:19]1[CH:24]=[CH:23][C:22]([S:3]([CH3:28])(=[O:5])=[O:2])=[CH:21][CH:20]=1)=[CH:12]/[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH3:8]

Participants

5

Reactant 3

HCID 180AcetoneHCID 23707502Potassium hydroxy sulfiteHCID 67084522(E)-3-Cyclohexyl-2-(4-methylsulfanyl-phenyl)-acrylic acid ethyl ester

Product 1

HCID 67084585(E)-3-Cyclohexyl-2-(4-methanesulfonyl-phenyl)-acrylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Add a suspension of oxone ® (33 g, 53 mmol) in water (300 mL) to a solution of (E)-3-cyclohexyl-2-(4-methylsulfanyl-phenyl)-acrylic acid ethyl ester (7.4 g, 24 mmol) in acetone (300 mL). Stir for three h, and then add water. Extract the resulting mixture with dichloromethane (2×500 mL). Combine the extracts, wash them with saturated aqueous sodium chloride solution, dry them over magnesium sulfate, and remove solvent under vacuum. Apply the residue to silica gel column, and elute this with a 15:15:70 mixture of dichloromethane: ethyl acetate: hexane to afford the title compound as an off-white solid (7.35 g). MS (m/e): 337 (M+H).

Workup

  1. additionAdd
  2. extractionExtract the resulting mixture with dichloromethane (2×500 mL)
  3. washCombine the extracts, wash them with saturated aqueous sodium chloride solution
  4. dry with materialdry them over magnesium sulfate
  5. customremove solvent under vacuum
  6. washApply the residue to silica gel column, and elute this
  7. additionwith a 15:15:70 mixture of dichloromethane

Sources & evidence

ORD record
ord-efd037e785214581b0673ed488c14e6f
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

Loading…