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

HRID 2213099노트

반응식

HRID 2213099 반응식
[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]

참가 물질

5

반응물 3

HCID 962WaterHCID 166653HydrideHCID 21956523HCID 21956523, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9774da904bc6423caac1cb8d54730f50
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07105533B2

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