4-Pentenoyl chloride → Nona-1,8-dien-5-one

Participants

Reaction Conditions

Reaction Steps

In an oven-dried 500 mL round-bottomed flask (t=g) was added 4-Pentenoyl chloride (6.04 mL, 54.7 mmol) in THF (80 mL) to give a tan solution. After cooling to −78° C., 3-Butenylmagnesium bromide (115 mL, 57.5 mmol) was added via syringe over 90 min. After warming to room temperature for 3 hours, the reaction was quenched with saturated NH4Cl solution. THF was stripped off and the remaining was extracted with EtOAc. The organic layer was washed with brine, dried with Na2SO4, and concentrated to a slightly yellow oil. Purification (two batches) by FCC up to 40% Et2O/hexane afforded the product as a colorless oil: (5.13 g, 68%). 1H NMR (400 MHz, CDCl3) δ 5.84-5.68 (m, 2H), 5.05-4.90 (m, 4H), 2.49 (t, J=7.4 Hz, 4H), 2.35-2.20 (m, 4H).

Provenance & Evidence