3-Acetoxy-2,2-dimethyl-1-propanesulfonamide → 3-Hydroxy-2,2-dimethylpropane-1-sulfonamide

HRID 465931Notes

Reaction equation

HRID 465931 reaction equation
C([O:4][CH2:5][C:6]([CH3:13])([CH3:12])[CH2:7][S:8]([NH2:11])(=[O:10])=[O:9])(=O)C.CO.C[O-].[Na+]>CO>[OH:4][CH2:5][C:6]([CH3:13])([CH3:12])[CH2:7][S:8]([NH2:11])(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 102625063-Acetoxy-2,2-dimethyl-1-propanesulfonamideHCID 23694274Sodium methanolate methanol

Product 1

HCID 103296873-Hydroxy-2,2-dimethylpropane-1-sulfonamideYield 77.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 10.0 g of 3-acetoxy-2,2-dimethyl-1-propanesulfonamide in 80 ml of methanol was added 9.2 g of 28 W/W % sodium methoxide methanol solution at room temperature with stirring. After stirring for 30 minutes, the reaction mixture was concentrated to dryness, and the residue was subjected to a silica gel column chromatography, eluting with chloroform-methanol (9:1). The corresponding fractions were concentrated to obtain 6.2 g of 3-hydroxy-2,2,-dimethyl-1-propanesulfonamide.

Workup

  1. stirringAfter stirring for 30 minutes
  2. concentrationthe reaction mixture was concentrated to dryness
  3. washeluting with chloroform-methanol (9:1)
  4. concentrationThe corresponding fractions were concentrated

Sources & evidence

ORD record
ord-1f814b9dbc544c2b900d8b8b6a030c56
Source dataset
uspto-grants-1992_10
Patent number
US05155108

Reaction notes

Loading…