Ethyl Acetate → 4-Tert-butyl-2-chloro-6-methylpyridine

HRID 1446719노트

반응식

HRID 1446719 반응식
P(Cl)(Cl)([Cl:3])=O.[C:6]([C:10]1[CH:15]=[CH:14][N+:13]([O-])=[C:12]([CH3:17])[CH:11]=1)([CH3:9])([CH3:8])[CH3:7].C(OCC)(=O)C>ClCCl>[Cl:3][C:14]1[CH:15]=[C:10]([C:6]([CH3:9])([CH3:8])[CH3:7])[CH:11]=[C:12]([CH3:17])[N:13]=1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 594853984-tert-Butyl-2-methyl-pyridine 1-oxide

생성물 1

HCID 601265994-Tert-butyl-2-chloro-6-methylpyridine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

Add phosphorus oxychloride (15 mL) to 4-tert-butyl-2-methyl-pyridine 1-oxide (2.00 g, 12.10 mmol) and heat to 100° C. for 36 hours. Evaporate off the excess phosphorus oxychloride. Treat the oil cautiously with ice and water with stirring and make basic by treatment with aqueous bicarbonate solution. Extract with dichloromethane (3×75 mL) and pool, desiccate, filter, and concentrated. Chromatograph the crude product on silica using a gradient of (0→5→8%) ethyl acetate in dichloromethane to afford the title compound (0.82 g, 4.46 mmol). MS (ESI), m/z 184 (M+1).

후처리

  1. customEvaporate off the excess phosphorus oxychloride
  2. additionTreat the oil cautiously with ice and water
  3. extractionExtract with dichloromethane (3×75 mL) and pool, desiccate
  4. filtrationfilter
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2d263cae928d4b339bb7ec3c197b9b7c
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666879B2

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