Ammonium Chloride → HCID 71662966, compound

HRID 2178140Notes

Reaction equation

HRID 2178140 reaction equation
[F:1][C:2]([F:14])([F:13])[CH:3]1[O:7][N:6]=[C:5]([C:8](OCC)=[O:9])[CH2:4]1.[BH4-].[Na+].[NH4+].[Cl-]>CCO>[F:14][C:2]([F:1])([F:13])[CH:3]1[O:7][N:6]=[C:5]([CH2:8][OH:9])[CH2:4]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 71662965HCID 71662965, compound

Product 1

HCID 71662966HCID 71662966, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 5-(trifluoromethyl)-4,5-dihydroisoxazole-3-carboxylate (1.0 g, 4.74 mmol) in EtOH (10 ml) was slowly added at 0° C. sodium borohydride (197 mg, 5.21 mmol) and the suspension was stirred at 0° C. for 4 h. The suspension was treated with half saturated aqueous NH4Cl, stirring was continued for 10 minutes, the mixture was extracted with diethylether, the organic layers were dried and evaporated (70 mbar/40° C.) to give crude (5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)methanol (803 mg) as a colorless oil which was used without further purification. MS: m/z=169 [M]+.

Workup

  1. stirringstirring
  2. waitwas continued for 10 minutes
  3. extractionthe mixture was extracted with diethylether
  4. customthe organic layers were dried
  5. customevaporated (70 mbar/40° C.)

Sources & evidence

ORD record
ord-de5c201257c94cf589f2712fb9230b47
Source dataset
uspto-grants-2015_06
Patent number
US09067926B2

Reaction notes

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