Sodium borohydride → {3-Methyl-5-[5-(trifluoromethyl)pyridin-2-yl]thien-2-yl}methanol

HRID 9658Notes

Reaction equation

HRID 9658 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=2)[S:4][C:3]=1[CH:17]=[O:18].[BH4-].[Na+]>O1CCCC1.O>[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=2)[S:4][C:3]=1[CH2:17][OH:18]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 219863063-Methyl-5-[5-(trifluoromethyl)pyridin-2-yl]thiophene-2-carbaldehyde2×

Product 1

HCID 21986475{3-Methyl-5-[5-(trifluoromethyl)pyridin-2-yl]thien-2-yl}methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-methyl-5-[5-(trifluoromethyl)pyridin-2-yl]thiophene-2-carbaldehyde (intermediate 78, 0.144 g) in tetrahydrofuran (10 ml) and water (15 ml) was treated with sodium borohydride (0.03 g). The reaction was stirred at room temperature for 30 minutes, extracted with ethyl acetate and the organic layer washed with water and dried with brine and over magnesium sulfate. The title compound was isolated after removal of the desiccant and evaporation of the solvent.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer washed with water
  3. dry with materialdried with brine and over magnesium sulfate

Sources & evidence

ORD record
ord-c4c7b667259941398d24acbf3497c507
Source dataset
uspto-grants-2006_08
Patent number
US07091237B2

Reaction notes

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