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

HRID 61415

Reaktionsgleichung

Reaktionsgleichung von HRID 61415
[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]

Komponenten

3

Edukt 2

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

Produkt 1

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

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2e9abcd6642b426286d808c86562dcfc
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440995B2

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