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

HRID 1498976Notes

Reaction equation

HRID 1498976 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]>>[N+:10]([CH2:13][CH:6]1[CH2:5][CH:4]([CH2:3][CH:2]=[CH2:1])[C:8](=[O:9])[CH2:7]1)([O-:12])=[O:11]

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, which previously had been rinsed with methanol and partially air dried), and heated to 60° C. for 2 h. The mixture was cooled to room temperature, diluted with methylene chloride (20 mL), and filtered. The filtrate was concentrated in vacuo, redissolved in minimum methylene chloride, and loaded onto a silica gel column (˜100 mL). Elution with methylene chloride afforded 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. washpreviously had been rinsed with methanol and partially air
  2. customdried), and
  3. temperatureThe mixture was cooled to room temperature
  4. additiondiluted with methylene chloride (20 mL)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. dissolutionredissolved in minimum methylene chloride
  8. washElution with methylene chloride

Sources & evidence

ORD record
ord-f577bd7024af453f8ea68989067b2748
Source dataset
uspto-grants-2015_12
Patent number
US09200011B2

Reaction notes

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