Iodine → HCID 55301267, compound

Participants

Reaction Steps

In a flame-dried flask, under an argon atmosphere, magnesium (7.8 g, 0.33 mol) and a small crystal of iodine in just enough THF to cover the magnesium was heated to a gentle reflux until the color had disappeared. Approximately 10% of a solution of 4-bromo-1-buten (32.5 mL, 0.321 mol) in THF (100 mL) was added all at once and reflux was continued until a brown coloration appeared. The remainder of the solution was added dropwise with continued reflux. After the addition was complete heating was maintained for 10 min, at which point almost all of the Mg had dissolved. The Grignard reagent solution was added to a second cooled (ice-bath) solution of 4-chloro-N-methoxy-N-methylbutanamide (21.3 g, 0.128 mol) in THF (200 mL). The resulting mixture was stirred for at room temperature for 2 h, poured into a mixture of ether and saturated aqueous ammonium chloride. The layers were separated and the aqueous phase was extracted with ether. The combined extracts were dried over Mg2SO4, filtered and concentrated under reduced pressure to give crude 1-chlorooct-7-en-4-one (17 g, 85%) as yellow liquid. 1H NMR (CDCl3, 500 MHz) δ 5.93-5.69 (m, 1H), 5.11-4.92 (m, 2H), 3.58 (t, J=6.5 Hz, 2H), 2.65-2.50 (m, 4H), 2.41-2.26 (m, 2H), 2.11-1.98 (qw, J=6.5 Hz, 2H).

Provenance & Evidence