Sodium hydride → HCID 86701116, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 26 (35 g, 78 mmol) (Prepared according to the synthesis of Example 3, step 4) in DMF (250 mL) was treated with NaH (70%, 8 g, 233 mmol) at 5° C. for 30 min, then Allyl-Br (28 g, 233 mmol) was added slowly. After stirring for 1.5 hours at 15° C., the reaction was quenched by H2O (300 mL), extracted with ethyl acetate (3×200 mL). The organic layers were collected, washed with brine (5×100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a residue, which was purified by a silica gel column, eluted with 5%˜10% ethyl acetate in petroleum ether to afford the title compound (32 g, 78%) as a yellow oil; (ES, m/z) [M+H]+ 529.1; 1H NMR (300 MHz, CDCl3) δ 6.07 (d, J=6.3 Hz, 1H), 5.85-6.05 (m, 2H), 5.15-5.38 (m, 4H), 4.22-4.30 (m, 4H), 4.02-4.07 (m, 2H), 3.76-3.78 (m, 2H), 3.60-3.62 (m, 1H), 3.48-3.52 (m, 1H), 3.31 (s, 3H), 1.55 (s, 9H), 0.93 (s, 9H), 0.08 (s, 6H).

Provenance & Evidence