Sodium borohydride → HCID 18324526, compound

HRID 1251901Notes

Reaction equation

HRID 1251901 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[CH3:15])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:16])[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[CH3:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18324431HCID 18324431, compound

Product 1

HCID 18324526HCID 18324526, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A cooled (ice-bath) solution of 1-(4-fluorophenyl)-2-(2-methylimidazol-1-yl)ethanone (9.0 g, 41.3 mmol) in methanol (60 ml) was treated portionwise with sodium borohydride (1.56 g; 41.3 mmol) and the mixture stirred at ambient temperature for 16 hours. Most of the methanol was removed and water and ethyl acetate added. The organic layer was separated, the aqueous extracted with ethyl acetate (2×) and the combined organic extracts washed with water, brine, dried filtered and evaporated to give a residue which was triturated with diethyl ether to give 1-(4-fluorophenyl)-2-(2-methylimidazol-1-yl)ethanol (7.7 g, 84%).

Workup

  1. customMost of the methanol was removed
  2. additionwater and ethyl acetate added
  3. customThe organic layer was separated
  4. extractionthe aqueous extracted with ethyl acetate (2×)
  5. washthe combined organic extracts washed with water, brine
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customto give a residue which
  10. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-157871880dae4fffbc1035b394a0c2eb
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

Loading…