Water → (3,5-Dimethylpyridin-4-yl)methanol

HRID 2054496Notes

Reaction equation

HRID 2054496 reaction equation
COC1C=CC(C[N:8]2[C:16]3[C:11](=[CH:12]C=[C:14](C(C4C=CC=CC=4)=O)[CH:15]=3)[C:10]([CH3:25])=[CH:9]2)=CC=1.[BH4-].[Na+].[OH2:30]>>[CH3:14][C:15]1[CH:16]=[N:8][CH:9]=[C:10]([CH3:25])[C:11]=1[CH2:12][OH:30]

Participants

4

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22663420[1-(4-methoxy-benzyl)-3-methyl-1H-indol-6-yl]-phenyl methanone

Product 1

HCID 22663284(3,5-Dimethylpyridin-4-yl)methanol

Procedure

A stirred solution of 3,5-dimethyl-pyridyl-4-carbaldehyde (2.3 g, Reference Example 24) in methylated spirit (50 ml), at room temperature and under nitrogen, was treated with powdered sodium borohydride (1.28 g). After stirring for 6 hours the resulting homogeneous solution was allowed to stand at room temperature for a further 12 hours then treated with water (10 ml). The reaction mixture was evaporated, then azeotroped with toluene. The residue was extracted three times with hot dichloromethane (100 ml). The combined extracts were evaporated to afford a white solid which was subjected to flash chromatography on silica, eluting with a mixture of ethyl acetate and pentane (1:1, v/v) to afford the title compound (1.2 g) as a white solid, m.p. 93-95° C.

Workup

  1. waitto stand at room temperature for a further 12 hours
  2. customThe reaction mixture was evaporated
  3. customazeotroped with toluene
  4. extractionThe residue was extracted three times with hot dichloromethane (100 ml)
  5. customThe combined extracts were evaporated
  6. customto afford a white solid which
  7. washeluting with a mixture of ethyl acetate and pentane (1:1

Sources & evidence

ORD record
ord-24c272c40202404daf97bfc92b03719e
Source dataset
uspto-grants-2008_02
Patent number
US07329675B2

Reaction notes

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