Nitromethane → 3-Nitromethyl-5-(propene-3-yl)cyclopentanone

HRID 590761

반응식

HRID 590761 반응식
[CH2:1]=[CH:2][CH2:3][CH:4]1[C:8](=[O:9])[CH:7]=[CH:6][CH2:5]1.[N+:10]([CH3:13])([O-:12])=[O:11]>>[CH2:3]([CH:4]1[CH2:5][CH:6]([CH2:13][N+:10]([O-:12])=[O:11])[CH2:7][C:8]1=[O:9])[CH:2]=[CH2:1]

참가 물질

3

반응물 2

HCID 6375NitromethaneHCID 134445455-(Prop-2-en-1-yl)cyclopent-2-en-1-one

생성물 1

HCID 675151713-Nitromethyl-5-(propene-3-yl)cyclopentanone수율 57%

반응 조건

온도
60 °C

실험 절차

A stirred solution of 5-(propene-3-yl)cyclopent-2-enone (0.428, 3.5 mmol) in nitromethane (2 mL) under nitrogen was treated with DOWEX® 550A-OH resin (0.80 g, rinsed with methanol and partially air dried), and heated to 60° C. for 2 h. The mixture was cooled to room temperature, diluted with dichloromethane (20 mL), and filtered. The filtrate was concentrated in vacuo, redissolved in minimum dichloromethane, and added to a silica gel column (˜100 cc) and eluted with dichloromethane to afford the subject compound (0.368 g, 57%) as a colorless oil. NMR (CDCl3): δ 5.65-5.80 (m, 1 H), 5.00-5.15 (m, 2 H), 4.40-4.50 (m, 2 H), 2.85-3.15 (m, 1 H), 2.30-2.70 (m, 4 H), 1.90-2.20 (m, 3 H). MS (M+1): 183.9.

후처리

  1. washrinsed with methanol and partially air
  2. customdried), and
  3. temperatureThe mixture was cooled to room temperature
  4. additiondiluted with dichloromethane (20 mL)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. dissolutionredissolved in minimum dichloromethane
  8. additionadded to a silica gel column (˜100 cc)
  9. washeluted with dichloromethane

출처 및 근거

ORD 기록
ord-ab2bb199fa29489780df1912b56ec506
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233985B2

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