(3,5-Dimethylpyridin-2-yl)methanol → 3,5-Dimethylpyridine-2-carbaldehyde

HRID 250956

반응식

HRID 250956 반응식
[CH3:1][C:2]1[C:3]([CH2:9][OH:10])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1>C(Cl)Cl.O=[Mn]=O>[CH3:1][C:2]1[C:3]([CH:9]=[O:10])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

참가 물질

4

반응물 1

HCID 10630548(3,5-Dimethylpyridin-2-yl)methanol

생성물 1

HCID 187316833,5-Dimethylpyridine-2-carbaldehyde

시약·촉매·용매 2

HCID 14801Manganese dioxide촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of (3,5-dimethyl-pyridin-2-yl)-methanol (2.12 g, 15.45 mmol) (Weidmann, K. et al. J. Med. Chem. 1992, 35, 438-450) in CH2Cl2 (50 mL) was added MnO2 (9.41 g, 108.18 mmol) and the reaction mixture was refluxed overnight. Then it was cooled and the mixture was filtered through a layer of celite. The filtrate was concentrated to afford a brown/yellow oil. Purification by flash column chromatography on silica gel using 30% EtOAc/hexane afforded 3,5-dimethyl-pyridine-2-carbaldehyde as a yellow oil (960 mg, 31% over 3 steps). 1H NMR (CDCl3) δ 2.39 (s, 3H), 2.62 (s, 3H), 7.41 (s, 1H), 8.47 (s, 1H), 10.15 (s, 1H).

후처리

  1. temperaturethe reaction mixture was refluxed overnight
  2. temperatureThen it was cooled
  3. filtrationthe mixture was filtered through a layer of celite
  4. concentrationThe filtrate was concentrated
  5. customto afford a brown/yellow oil
  6. customPurification by flash column chromatography on silica gel using 30% EtOAc/hexane

출처 및 근거

ORD 기록
ord-727f3f24a0a64931b81c617c484e059c
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863293B2

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