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

HRID 33541ノート

反応式

HRID 33541 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f2455bc280594cd2a7a7ddd2238e694e
出典データセット
uspto-grants-2008_09
特許番号
US07429605B2

反応ノート

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