Water → ethyl (RS)-alpha-[(tert-butylsulfonyl)methyl]hydrocinnamate

HRID 478031Notes

Reaction equation

HRID 478031 reaction equation
[CH2:1]([O:3][C:4](=S)[CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6]C(C)(C)C)[CH3:2].O[O:20][S:21]([O-:23])=O.[K+].[K].[OH2:26]>CO>[CH2:1]([O:3][C:4](=[O:26])[CH:5]([CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:6][S:21]([C:5]([CH3:11])([CH3:6])[CH3:4])(=[O:23])=[O:20])[CH3:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 5462222PotassiumHCID 23707502Potassium hydroxy sulfiteHCID 566056972-Benzyl-3-tert.-butylthiopropionic acid ethyl ester

Product 1

HCID 14158057ethyl (RS)-alpha-[(tert-butylsulfonyl)methyl]hydrocinnamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.5 g of 2-benzyl-3-tert.-butylthio-propionic acid ethyl ester is dissolved in 8 ml of methanol and, while cooling with ice, 1.63 g of oxone® (potassium peroxomonosulphate, 50% KHSO5, Ventron GmbH, Karlsruhe) in 7 ml of water are added and the whole is stirred overnight at room temperature. The solution is diluted with water and extracted with methylene chloride, and the extracts are dried and concentrated by evaporation. 1H-NMR (DMSO-d6): 1.0 ppm (t, 3H), 1.3 (s, 9H); 2.8-3.5 (m, 5H), 3.95 (q, 2H); 7.15-7.3 (m, 5H).

Workup

  1. additionare added
  2. extractionextracted with methylene chloride
  3. customthe extracts are dried
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-8a9feac9444e41fc88cdabd622217bc8
Source dataset
uspto-grants-1989_12
Patent number
US04889869

Reaction notes

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