Pyridine → 3-Acetoxycyclohexene

HRID 337182노트

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HRID 337182 반응식
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.N1C=CC=CC=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>>[C:14]([O:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1)(=[O:16])[CH3:15]

참가 물질

4

반응물 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 131982-Cyclohexen-1-OL

생성물 1

HCID 111161483-Acetoxycyclohexene수율 94%

반응 조건

온도
0 °C

실험 절차

To a solution of 2-cyclohexen-1-ol (16) (45.5 mmol, 5.02 mL) in pyridine (0.27 mol, 22 mL) at 0° C., acetic anhydride was added dropwise and the reaction mixture was stirred at 0° C. for ½ h. The ice bath was removed, and the mixture was stirred at room temperature overnight. The mixture was diluted with EtOAc, washed with HCl (1 N), saturated NaHCO3, brine, and concentrated in vacuo to give 6 g (94%) of the crude product 17 which was used in the next step without further purification. TLC with 20% EtOAc/Hexane, stained with 5% H2SO4/EtOH, Rf for (16): 0.4, Rf for (17): 0.8.

후처리

  1. customThe ice bath was removed
  2. stirringthe mixture was stirred at room temperature overnight
  3. additionThe mixture was diluted with EtOAc
  4. washwashed with HCl (1 N), saturated NaHCO3, brine
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9b69b1c899954ecc88c475798102edee
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889719B2

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