Tetrahydrofuran → 1-(But-3-en-1-yloxy)-2-methylidenecyclohexane

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyltriphenylphosphonium bromide (22.30 g, 62.4 mmol) in THF (125 mL) at rt was added sodium hexamethyldisilylazide (2M in THF, 31.2 mL, 62.4 mmol) dropwise. The mixture was heated to 60° C. for 1 hr. 2-(but-3-en-1-yloxy)cyclohexanone (7.0 g, 41.6 mmol.) was then added and the mixture was stirred at 60° C. for 3 hr. The reaction was cooled to rt, quenched with sat'd. aq.NH4Cl, and extracted with Et2O. The combined organics were dried filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 5.78-5.90 (m, 1H), 5.00-5.13 (m, 2H), 4.82 (s, 1H), 4.78 (s, 1H), 3.74 (dd, 1H, J=3.9 Hz, 6.3 Hz), 3.35-3.49 (m, 2H), 1.12-2.38 (m, 10H).

Provenance & Evidence