2-Cyclohexen-1-one → HCID 24794625, compound

HRID 2260154Notes

Reaction equation

HRID 2260154 reaction equation
[C:1]1([CH2:7][CH:8]=[N+:9]([O-:11])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]1(=[O:18])[CH2:17][CH2:16][CH2:15][CH:14]=[CH:13]1>>[CH2:7]([C@@H:8]1[C@@H:13]2[C:12](=[O:18])[CH2:17][CH2:16][CH2:15][C@@H:14]2[O:11][N:9]1[CH3:10])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 135942-Cyclohexen-1-one2×HCID 75577546HCID 75577546, compound

Product 1

HCID 24794625HCID 24794625, compoundYield 75%

Conditions

Temperature
100 °C

Procedure

In a dry sealed tube under N2 were placed N-(2-phenylethylidene)methylamine N-oxide (2.0 g, 13.4 mmol) and 2-cyclohexenone (5 ml). The reagents were stirred at 100° C. for 15 hours. Unreacted 2-cyclohexenone was removed by Kugelrohr distillation to yield the crude product as a viscous brown oil (K100%). The crude product was purified by flash chromatography on silica gel (Sorbsil C60, 60A) using 60:40 v/v petroleum ether (fraction of bp 40°-60° C.):ethyl acetate as the solvent system to give the unsubstituted title compound as an orange oil (2.48 g. 75%), νmax (film) 2944, 2872, 1709, 1455, 1238 cm-1 ; δH (250 MHz, CDCl3 --Me4Si) 1.75-1.95 (4H, br m), 2.20-2.40 (2H, br m), 2.50 (3H, s), 3.70-3.80 (1H, t), 2.85-2.95 (2H, t), 3.45-3.55 (1H, br m), 4.30-4.40 (1H, br m), 7.15-7.30 (5H, br m), M/z 246 (MH+ 100%) (Found: MH+ 246.149; C15H19NO2 requires MH+ 246.1522).

Workup

  1. customIn a dry sealed tube under N2
  2. customwas removed by Kugelrohr distillation
  3. customto yield the crude product as a viscous brown oil (K100%)
  4. customThe crude product was purified by flash chromatography on silica gel (Sorbsil C60, 60A)

Sources & evidence

ORD record
ord-4e68e8b28db540b488bf5a69c0a2fa75
Source dataset
uspto-grants-1995_12
Patent number
US05476867

Reaction notes

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