Allyl bromide → 2-[(Prop-2-en-1-yloxy)methyl]cyclohexanone

Participants

Reaction Steps

To a mixture of NaH (1.14 g, 60% oil dispersion, 28.6 mmol) in dry THF (45 mL) at 0° C. was added 1,4-dioxaspiro[4.5]dec-6-ylmethanol (2.46 g, 14.3 mmol) in dry THF (5 mL). The mixture was allowed to warm to rt and stirred for 1 hr. The mixture was then cooled to 0° C. and allyl bromide (2.10 mL, 24.28 mmol) was added in one portion. The mixture was then allowed to warm to rt and stirred for 1 hr. The mixture was then heated to 60° C. overnight. It was cooled to 0° C. and quenched with 50 mL of 10% aq HCl. This mixture was stirred for 1 hr at rt. The resulting mixture was cooled to 0° C. and neutralized carefully with solid Na2CO3 and then 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 5.86-5.95 (m, 1H), 5.28 (d, 1H, J=1.7 Hz), 5.25 (d, 1H, J=1.5 Hz), 5.17 (d, 1H, J=10.5 Hz), 3.94-4.03 (m, 2H), 3.79 (dd, 1H, J=5.1 Hz, 9.8 Hz), 3.38 (dd, 1H, J=7.33 Hz, 9.53 Hz), 2.56-2.65 (m, 1H), 2.26-2.43 (m, 3H), 2.02-2.10 (m, 1H), 1.85-1.93 (m, 1H), 1.61-1.74 (m, 2H), 1.39-1.49 (m, 1H).

Provenance & Evidence