Sodium borohydride → HCID 54050151, compound

HRID 342951Notes

Reaction equation

HRID 342951 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-8232f34c3ae64ed19992bd2ecc1e99a6
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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