Pyridine → Cyclopent-3-en-1-yl methanesulfonate

HRID 222213노트

반응식

HRID 222213 반응식
[CH:1]1([OH:6])[CH2:5][CH:4]=[CH:3][CH2:2]1.N1C=CC=CC=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>C(Cl)Cl>[CH3:13][S:14]([O:6][CH:1]1[CH2:5][CH:4]=[CH:3][CH2:2]1)(=[O:16])=[O:15]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 31297Methanesulfonyl chloride2회HCID 2814783-Cyclopenten-1-ol

생성물 1

HCID 12174535Cyclopent-3-en-1-yl methanesulfonate수율 68.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
35 °C

실험 절차

3-Cyclopentene-1-ol (0.500 g, 5.94 mmol) was stirred in DCM (95 mL). Pyridine (2.40 mL), N,N-dimethylaminopyridine (0.10 g, 1.00 mmol) and methanesulfonyl chloride (0.690 mL, 8.92 mmol) were added, and the reaction mixture was stirred at 35° C. for 4 h. N,N-Dimethylaminopyridine (0.14 g, 1.2 mmol) and methanesulfonyl chloride (0.69 mL, 8.92 mmol) were added, and the reaction was stirred overnight. TLC indicated complete conversion. The reaction mixture was cooled and concentrated. The residue was purified by silica gel chromatography, eluting with DCM, to afford the title compound as a clear oil (0.660 g, 68%).

후처리

  1. stirringthe reaction was stirred overnight
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with DCM

출처 및 근거

ORD 기록
ord-b980014275ae42bab0211f78cfe46a2a
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207177B2

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