Water → 3-Methoxy-4-pyridin-2-ylbenzaldehyde

HRID 2213099ノート

反応式

HRID 2213099 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[C:6]#N.[H-].[OH2:18]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[CH:6]=[O:18]

参加物

5

反応物 3

HCID 962WaterHCID 166653HydrideHCID 21956523HCID 21956523、化合物

生成物 1

HCID 219565123-Methoxy-4-pyridin-2-ylbenzaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

A solution of 3-methyoxy-4-pyridin-2-ylbenzonitrile (600 mg, 2.64 mmol) in CH2Cl2 (10 mL) was cooled to −78° C. and was treated with diisobutylalumnium hydride (3.2 mL of 1M in CH2Cl2, 3.2 mmol). After stirring the reaction mixture at −78° C. for 2 h, the temperature was raised to −40° C. before quenching the reaction with a mixture of silica gel (6 g) and water (2 mL) and then warmed to rt. The reaction mixture was dried (K2CO3 and MgSO4), and concentrated. The residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:4 to 1:1) to afford 3-methoxy-4-pyridin-2-ylbenzaldehyde.

後処理

  1. temperaturethe temperature was raised to −40° C.
  2. custombefore quenching
  3. customthe reaction
  4. temperaturewarmed to rt
  5. dry with materialThe reaction mixture was dried (K2CO3 and MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:4 to 1:1)

出典と根拠

ORDレコード
ord-9774da904bc6423caac1cb8d54730f50
出典データセット
uspto-grants-2006_09
特許番号
US07105533B2

反応ノート

読み込み中…