Ammonium Chloride → 7-(5'-Fluoro-2'-methoxyphenyl)hept-1-en-5-ol

Participants

Reaction Steps

To a solution of 4 (3.0 g, 19.5 mmol) in THF (20 mL) at 0° C. was added a solution 1-butenylmagnesium bromide (0.5 M in THF, 45 mL, 22.5 mmol) dropwise for 15 min. The reaction mixture was poured into a solution of saturated ammonium chloride (80 mL) in a separatory funnel. The organic fraction was extracted with EtOAc (3×60 mL) and the combined organic layers were washed with brine (50 mL) and dried over sodium sulfate. The product was purified by flash column chromatography (EtOAc/hexane, 15:85, v:v, Rf=0.2) to give the product as a colorless oil (3.7 g, 94%); 1H NMR (CDCl3, 500 MHz): δ 6.86-6.82 (m, 2 H), 6.76 (dd, J=4.6, 8.6 Hz, 1 H), 5.82 (m, 1 H), 5.04 (d, J=17.3 Hz, 1 H), 4.95 (d, J=10.2 Hz, 1 H), 3.81 (s, 3 H), 3.55 (m, 1 H), 2.75-2.69 (m, 2 H), 2.2 (m, 1 H), 2.1 (m, 1 H), 1.96 (bs, 1 H), 1.73-1.68 (m, 2 H), 1.6-1.53 (m, 3 H).

Provenance & Evidence