Aluminium lithium hydride → 5-(Hydroxymethyl)-2-((5-(trifluoromethyl)pyridin-2-yl)oxy)benzonitrile

HRID 474630ノート

反応式

HRID 474630 の反応式
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=2)=[C:6]([C:21]#[N:22])[CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.O>[OH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:13][N:12]=2)=[C:6]([CH:5]=1)[C:21]#[N:22]

参加物

5

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 668253413-Cyano-4-(5-trifluoromethyl-pyridin-2-yloxy)-benzoic acid methyl ester

生成物 1

HCID 668256575-(Hydroxymethyl)-2-((5-(trifluoromethyl)pyridin-2-yl)oxy)benzonitrile収率 60.7%

試薬・触媒・溶媒 2

HCID 962Water触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-55 °C

実験手順

To a solution of 3-cyano-4-(5-trifluoromethyl-pyridin-2-yloxy)-benzoic acid methyl ester (23 g, 0.070 mol) in anhydrous THF (200 mL) was added portionwise LiAlH4 (4.07 g, 0.11 mmol) at −78° C. The reaction mixture was warmed to −55° C. slowly and stirred for 20 mins, diluted with water (3 mL 0.16 mmol, slow addition), filtered and concentrated. Purification via column chromatography on silica gel (petroleum ether/ethyl acetate=10/1 to 5/1) afforded the title product (12.5 g) as a colorless oil. LCMS: rt=2.81 min, [M+H+]=295.

後処理

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customPurification via column chromatography on silica gel (petroleum ether/ethyl acetate=10/1 to 5/1)

出典と根拠

ORDレコード
ord-eb2076152c6c4185b57b9e794c73f997
出典データセット
uspto-grants-2014_01
特許番号
US08637536B2

反応ノート

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