1,3-Cyclohexadiene → HCID 19000049, compound

HRID 2260156Notes

Reaction equation

HRID 2260156 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.[CH:12]1[CH2:17][CH2:16][CH:15]=[CH:14][CH:13]=1>>[CH2:7]([CH:8]1[CH:17]2[CH:12]=[CH:13][CH2:14][CH2:15][CH:16]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 116051,3-CyclohexadieneHCID 75577546HCID 75577546, compound

Product 1

HCID 19000049HCID 19000049, compoundYield 87%

Procedure

N-(2-Phenylethylidene)methylamine N-oxide (797 mg, 5.34 mmol) and 1,3-cyclohexadiene (3 ml) were heated together at 70° C. in a sealed tube under nitrogen for 14 hours. The solution was cooled to room temperature and the excess 1,3-cyclohexadiene was removed under reduced pressure to yield a viscous oil (1.07 g, 87%). This crude product was purified by flash chromatography using 60:40 v/v petroleum ether (fraction of bp 40°-60° C.):ethyl acetate as the solvent system to give the title compound (Rf=0.34) as a pale yellow oil (375 mg, 35%), νmax (film) 3030, 2920, 2840, 1605, 1495, 1455, 1090 cm-1 ; δH (400 MHz; CDCl3 --Me4Si) 1.80-2.00 (4H, br m), 2.20-2.25 (1H, m), 2.60-2.65 (3H, s), 2.75-2.95 (2H and 1H, m), 4.20-4.25 (1H, br), 5.6-6.0 (2H, br m), 7.20-7.30 (5H, br m); M/z 229 (MH+ 100%) (Found: MH+ 230.1545; C15H19NO requires MH+ 230.1574).

Workup

  1. customthe excess 1,3-cyclohexadiene was removed under reduced pressure

Sources & evidence

ORD record
ord-96e9860ea6474c00bf9c397f23f7bd1c
Source dataset
uspto-grants-1995_12
Patent number
US05476867

Reaction notes

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