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

HRID 590761

Reaction equation

HRID 590761 reaction equation
[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]

Participants

3

Reactant 2

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

Product 1

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

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ab2bb199fa29489780df1912b56ec506
Source dataset
uspto-grants-2016_01
Patent number
US09233985B2

Linked notes

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