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

HRID 61415ノート

反応式

HRID 61415 の反応式
[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]

参加物

3

反応物 2

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

生成物 1

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

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2e9abcd6642b426286d808c86562dcfc
出典データセット
uspto-grants-2016_09
特許番号
US09440995B2

反応ノート

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