Sodium borohydride → {5-[4-(Trifluoromethyl)phenyl]isoxazol-3-yl}methan-1-ol

HRID 1296040Notes

Reaction equation

HRID 1296040 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[O:8][N:7]=1)=O)C.[BH4-].[Na+]>C1COCC1.CO>[F:20][C:17]([F:18])([F:19])[C:14]1[CH:13]=[CH:12][C:11]([C:9]2[O:8][N:7]=[C:6]([CH2:4][OH:3])[CH:10]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22064085Ethyl 5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylate

Product 1

HCID 22064161{5-[4-(Trifluoromethyl)phenyl]isoxazol-3-yl}methan-1-olYield 98.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 13A (14.1 g, 49.4 mmol) in 3:1 THF/MeOH, was treated with NaBH4 (5.6 g, 148 mmol) at ambient temperature. The reaction was then stired for 3H, followed by concentrating in vacuo to about 50 mL, quenching with 2 M HCl, extract 1×150 mL EtOAC, dry (Na2SO4) and concentrate in vacuo to give 11.8 g of the title compound pure enough for subsequent use. MS m/z 244 (M+1).

Workup

  1. concentrationby concentrating in vacuo to about 50 mL
  2. customquenching with 2 M HCl
  3. extractionextract 1×150 mL EtOAC
  4. dry with materialdry (Na2SO4)
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-08d78c0184ec4ad8a72d3eebea3a92e0
Source dataset
uspto-grants-2007_07
Patent number
US07244763B2

Reaction notes

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