2-Cyclohexen-1-one → HCID 54269430, compound

HRID 2260157Notes

Reaction equation

HRID 2260157 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]=[N+:10]([O-:12])[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]1(=[O:19])[CH2:18][CH2:17][CH2:16][CH:15]=[CH:14]1>>[CH3:11][N:10]1[C@H:9]([CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C@@H:14]2[C:13](=[O:19])[CH2:18][CH2:17][CH2:16][C@@H:15]2[O:12]1

Participants

3

Reactant 2

HCID 135942-Cyclohexen-1-oneHCID 85271769HCID 85271769, compound

Product 1

HCID 54269430HCID 54269430, compoundYield 89%

Procedure

N-(3-Phenylpropylidene)methylamine N-oxide (1.50 g, 9.19 mmol) and 2-cyclohexenone (5 ml) were heated at 80°-90° C. for 24 hours in a sealed tube under nitrogen. The solution was cooled to room temperature and the excess 2-cyclohexenone was removed under reduced pressure using Kugelrohr distillation to yield the crude product as a dark yellow oil (2.36 g, 99%). The crude product was purified by flash chromatography using 60:40 v/v light petroleum (fraction of bp 40°-60° C.):ethyl acetate as the solvent system to give the title compound as a colourless oil (2.11 g, 89%), vmax (film) 2941, 2872, 1710, 1454, 1235 cm-1 ; δH (250 MHz, CDCl3 --Me4Si) 1.70-2.0 (6H, br m), 2.25-2.55 (2H, m), 2.60-2.80 (2H, m), 2.70 (3H, s), 2.75 (1H, t), 3.25 (1H, br m), 4.45 (1H, br m), 7.10-7.30 (5H, br m); M/z 259 (M+ 100%) (Found: M+ 259.1572; C16H21NO2 requires M+ 259.1603).

Workup

  1. customthe excess 2-cyclohexenone was removed under reduced pressure
  2. distillationKugelrohr distillation
  3. customto yield the crude product as a dark yellow oil (2.36 g, 99%)
  4. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-b1188aa9fccf40ad98493888849dbf30
Source dataset
uspto-grants-1995_12
Patent number
US05476867

Reaction notes

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