Sodium borohydride → (4-(Trifluoromethyl)-1,3-thiazol-2-yl)methanol

HRID 1497399Notes

Reaction equation

HRID 1497399 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:16])([F:15])[C:5]1[N:6]=[C:7]([C:10](OCC)=[O:11])[S:8][CH:9]=1>CO>[F:16][C:4]([F:3])([F:15])[C:5]1[N:6]=[C:7]([CH2:10][OH:11])[S:8][CH:9]=1

Participants

4

Procedure

Sodium tetrahydroborate (840 mg) was added to a solution of ethyl 4-(trifluoromethyl)-1,3-thiazole-2-carboxylate (2.5 g) in methanol (15 ml) at 0° C., and the mixture was stirred at the same temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (1.7 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c3705374585541c890b69f84e6009047
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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