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

HRID 33533Notes

Reaction equation

HRID 33533 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH:7]=[N:6][CH:5]=1.[BH4-].[Na+]>C(O)C>[Cl: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 20099851Methyl 5-(4-chlorophenyl)nicotinate

Product 1

HCID 24729853(5-(4-Chlorophenyl)pyridin-3-yl)methanolYield 68.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 900 mg (3.49 mmol) 5-(4-Chloro-phenyl)-nicotinic acid methyl ester in 30.0 ml Ethanol was treated at room temperature (r. t.) with 264 mg (69.9 mmol) of sodium borohydride. The mixture was stirred for 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 6:1) gave 522 mg (67%) of [5-(4-Chloro-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-f884a7a13b014bd7be0032f745530dc0
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Reaction notes

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