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

HRID 33541Notes

Reaction equation

HRID 33541 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[CH:7]=[N:6][CH:5]=1.[BH4-].[Na+]>C(O)C>[Cl:16][C:12]1[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][CH:13]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20099850Methyl 5-(3-chlorophenyl)nicotinate

Product 1

HCID 24729846(5-(3-Chlorophenyl)pyridin-3-yl)methanolYield 29.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 1.0 g (4.04 mmol) 5-(3-Chloro-phenyl)-nicotinic acid methyl ester in 60.0 ml Ethanol was treated at room temperature (r. t.) with 304 mg (80.7 mmol) of sodium borohydride. The mixture was stirred over night 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/n-heptane 1:1) gave 261 mg (26%) of [5-(3-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-f2455bc280594cd2a7a7ddd2238e694e
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Reaction notes

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