Sodium borohydride → (5-(4-(Trifluoromethyl)phenyl)pyridin-3-yl)methanol

HRID 33521Notes

Reaction equation

HRID 33521 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[CH:7]=[N:6][CH:5]=1.[BH4-].[Na+]>C(O)C>[F:18][C:16]([F:17])([F:19])[C:13]1[CH:12]=[CH:11][C:10]([C:8]2[CH:9]=[C:4]([CH2:3][OH:2])[CH:5]=[N:6][CH:7]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20099855Methyl 5-(4-(trifluoromethyl)phenyl)nicotinate

Product 1

HCID 1519486(5-(4-(Trifluoromethyl)phenyl)pyridin-3-yl)methanolYield 65.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 335 mg (1.17 mmol) 5-(4-Trifluoromethyl-phenyl)-nicotinic acid methyl ester in 10.0 ml ethanol was treated at room temperature (r. t.) with 44 mg (1.17 mmol) of sodium borohydride. The mixture stirred two days at 50° C. Then it was poured on ice and extracted tree times with ethyl acetate. The combined organic phases were washed with water, dried (sodium sulphate) and evaporated. Chromatography on silica (eluent: ethyl acetate/methanol 5:1) gave 195 mg (64%) of [5-(4-Trifluoromethyl-phenyl)-pyridin-3-yl]-methanol.

Workup

  1. additionThen it was poured on ice
  2. extractionextracted tree times with ethyl acetate
  3. washThe combined organic phases were washed with water
  4. dry with materialdried (sodium sulphate)
  5. customevaporated

Sources & evidence

ORD record
ord-e9070980bb7a4af4980a657c08557dec
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Reaction notes

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