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

HRID 33528Notes

Reaction equation

HRID 33528 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)[CH:7]=[N:6][CH:5]=1.[BH4-].[Na+]>C(O)C>[F:20][C:17]([F:18])([F:19])[O:16][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 580025915-(4-Trifluoromethoxy-phenyl)-nicotinic acid methyl ester

Product 1

HCID 24729847(5-(4-(Trifluoromethoxy)phenyl)pyridin-3-yl)methanolYield 33.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 535 mg (1.76 mmol) 5-(4-Trifluoromethoxy-phenyl)-nicotinic acid methyl ester in 16 ml Ethanol was treated at room temperature (r. t.) with 67 mg (1.76 mmol) of sodium borohydride. The mixture was stirred for 4 h. at r. t., then two days at 80° C. The mixture 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 159 mg (33%) of [5-(4-Trifluoromethoxy-phenyl)-pyridin-3-yl]-methanol.

Workup

  1. customtwo days
  2. customat 80° C
  3. additionThe mixture was poured on ice
  4. extractionextracted tree times with ethyl acetate
  5. washThe combined organic phases were washed with water
  6. dry with materialdried (sodium sulphate)
  7. customevaporated

Sources & evidence

ORD record
ord-d96599b542d2457c84ac0aa46c7c899b
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Reaction notes

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