Sodium → 1-(1-Imidazolyl)-3-phenylsulfonyl-propan-2-ol

HRID 746001Notes

Reaction equation

HRID 746001 reaction equation
[N:1]1([CH2:6][C:7](=[O:18])[CH2:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:4][N:3]=[CH:2]1.[Na]>CO>[N:1]1([CH2:6][CH:7]([OH:18])[CH2:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:10])=[O:11])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 136889551-(1-Imidazolyl)-3-phenylsulfonylpropan-2-one

Product 1

HCID 136889561-(1-Imidazolyl)-3-phenylsulfonyl-propan-2-olYield 88.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred mixture of 10 g (0.0377 mole) 1-(1-imidazolyl)-3-phenylsulfonylpropan-2-one (the product of Example 11) in 50 ml methanol cooled in an ice-water bath, 0.9 g (0.0237 mole) sodium borhydride, was added in 5 portions. The reaction mixture became viscous, and methanol (100 ml) was added. The reaction mixture was allowed to come to room temperature and to stir for about 11/2 hours. The reaction mixture was cooled in an ice-water bath and the product removed by filtration. The precipiate was dried under vacuum to give 8.9 g of the above-identified product as an off-white solid, melting point 153°-156° C.

Workup

  1. temperaturecooled in an ice-water bath
  2. customto come to room temperature
  3. temperatureThe reaction mixture was cooled in an ice-water bath
  4. customthe product removed by filtration
  5. customThe precipiate was dried under vacuum

Sources & evidence

ORD record
ord-f1a8da68e6714af88f2016ad0587d8dc
Source dataset
uspto-grants-1986_07
Patent number
US04602030

Reaction notes

Loading…