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

HRID 2054496노트

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HRID 2054496 반응식
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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-24c272c40202404daf97bfc92b03719e
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07329675B2

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