Methanesulfonyl chloride → Cyclopent-3-en-1-yl methanesulfonate

HRID 2095658노트

반응식

HRID 2095658 반응식
[CH:1]1([OH:6])[CH2:5][CH:4]=[CH:3][CH2:2]1.[CH3:7][S:8](Cl)(=[O:10])=[O:9].C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:1]1([O:6][S:8]([CH3:7])(=[O:10])=[O:9])[CH2:5][CH:4]=[CH:3][CH2:2]1

참가 물질

6

반응물 3

HCID 31297Methanesulfonyl chlorideHCID 2814783-Cyclopenten-1-olHCID 516892Sodium Bicarbonate

생성물 1

HCID 12174535Cyclopent-3-en-1-yl methanesulfonate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-cyclopentene-1-ol (9.00 g, 107 mmol) in dry methylene chloride (150 mL) was added TEA (23.0 mL, 160 mmol) followed by DMAP (100 mg). To this solution was added methanesulfonyl chloride (14.72 g, 128 mmol) at 10-20° C. slowly over 15 minutes and stirred overnight at room temperature. To the reaction mixture was added aqueous saturated NaHCO3 (50 mL) and stirred for 15 minutes at room temperature. The organic layer was separated, washed with water, followed by brine and dried over NaSO4. It was filtered and concentrated to give the title compound as an oil that was used without purification in the next reaction. 1H NMR (300 MHz, CDCl3): δ=5.72 (s, 2H), 5.38 (mc, 1H), 3.00 (s, 3H), 2.81-2.61 (m, 4H).

후처리

  1. stirringstirred for 15 minutes at room temperature
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over NaSO4
  5. filtrationIt was filtered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c835edfa74f9458a9867ddd8c7f891e2
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445510B2

반응 노트

불러오는 중…