Ethanol → 4-(3-Pyridylmethyl)benzyl alcohol

HRID 1680029Notes

Reaction equation

HRID 1680029 reaction equation
COC(=O)/C=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:8][CH:7]=1.[BH4-].[Na+].C([OH:24])C>>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH2:12][C:9]2[CH:10]=[CH:11][C:6]([CH2:5][OH:24])=[CH:7][CH:8]=2)[CH:14]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 12882181(E)-3-[4-(3-Pyridylmethyl)phenyl]acrylic acid methyl ester

Product 1

HCID 128821784-(3-Pyridylmethyl)benzyl alcohol

Procedure

A mixture of 0.41 g of the aldehyde (prepared as described in Reference Example 1), 8 ml of ethanol and 78 mg of sodium borohydride was stirred at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate, washed with water, and a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a 4% V/V solution of ethanol in chloroform as eluent to give 0.33 g of the title compound having the following physical characteristics:

Workup

  1. washwashed with water
  2. dry with materiala saturated aqueous solution of sodium chloride, dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel using a 4% V/V solution of ethanol in chloroform as eluent

Sources & evidence

ORD record
ord-c53ae053dece442099e43fcfebace3c6
Source dataset
uspto-grants-1981_06
Patent number
US04271170

Reaction notes

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