Sodium borohydride → HCID 54050151, compound

HRID 266504Notes

Reaction equation

HRID 266504 reaction equation
[N+:1]([C:4]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:5]=1[C:6]([C:8]1[CH:9]=[N:10][O:11][C:12]=1[CH:13]1[CH2:15][CH2:14]1)=[O:7])([O-:3])=[O:2].[BH4-].[Na+]>C(O)C>[OH:7][CH:6]([C:5]1[CH:16]=[CH:17][C:18]([C:20]([F:22])([F:21])[F:23])=[CH:19][C:4]=1[N+:1]([O-:3])=[O:2])[C:8]1[CH:9]=[N:10][O:11][C:12]=1[CH:13]1[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 54345374HCID 54345374, compound

Product 1

HCID 54050151HCID 54050151, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[2-nitro-4-trifluoromethylbenzoyl]-5-cyclopropylisoxazole (8.00 g) and sodium borohydride (0.53 g) in ethanol (250 ml) was stirred at room temperature for 2 hours. The solution was evaporated almost to dryness and the resultant solution was diluted with ethyl acetate. The solution was washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness. The residue was purified by chromatography on silica eluted with a mixture of ether and petroleum ether to give 4-[hydroxy-(2-nitro-4-trifluoromethylphenyl)methyl]-5-cyclopropylisoxazole (compound 294, 5.95 g) as an off white solid: m.p. 76° C.

Workup

  1. customThe solution was evaporated almost to dryness
  2. additionthe resultant solution was diluted with ethyl acetate
  3. washThe solution was washed with water
  4. dry with materialdried (anhydrous magnesium sulphate)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customThe residue was purified by chromatography on silica
  8. washeluted with a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-794389ac2aff452baa89887ea08c0617
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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