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

HRID 380420ノート

反応式

HRID 380420 の反応式
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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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, map. 93-95° C.

後処理

  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

出典と根拠

ORDレコード
ord-0cfdb3858bfe4f7cba79b044f1bab39a
出典データセット
uspto-grants-2001_10
特許番号
US06303600B1

反応ノート

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