Sodium borohydride → 2-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propan-1-ol

HRID 490738Notes

Reaction equation

HRID 490738 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[S:5][C:6]=1[CH:7]([CH3:10])[CH:8]=[O:9].[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[S:5][C:6]=1[CH:7]([CH3:10])[CH2:8][OH:9]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 587657492-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propionaldehyde

Product 1

HCID 587657612-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propan-1-olYield 99.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propionaldehyde (2.0 g, 6.68 mmol) in ethanol (30 mL) is added to NaBH4 (0.25 g, 6.6 mmol) in portions at 0° C. The reaction is kept at 0° C. for 15 minutes and warmed up to room temperature for 2 hours. The reaction is quenched using water, extracted with ethyl acetate, dried over sodium sulfate. Concentration and column chromatography on silica gel eluted with hexanes and ethyl acetate yields the title compound (2.0 g).

Workup

  1. customThe reaction is quenched
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationConcentration and column chromatography on silica gel
  5. washeluted with hexanes and ethyl acetate

Sources & evidence

ORD record
ord-c24b3f88d80a4346bf8531c0eb30640d
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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