Sodium hydride → HCID 69085336, compound

Participants

Reaction Steps

A solution of 132 (12 g, 21 mmol) in DMF (60 mL) was treated with sodium hydride (2.9 g, 84 mmol, 70% dispersed by mineral oil) for 30 minutes at 0° C., followed by addition of PMBBr (25 g, 126 mmol). After additional 1.5 hours at 15° C., the reaction was quenched with water (200 mL), and extracted with dichloromethane (3×100 mL). The combined organic layer was washed with brine (3×50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluted with 5%-20% ethyl acetate in petroleum ether to afford 133 as light yellow oil (8.5 g, 50%). (ES, m/z) [M+H]+ 809.0; 1H NMR (300 MHz, CDCl3) δ 7.21-7.34 (m, 9H), 6.82-6.89 (m, 4H), 6.08 (d, J=6.3 Hz, 1H), 4.52-4.57 (m, 4H), 4.50 (s, 2H), 4.33-4.35 (m, 1H), 4.05-4.06 (m, 1H), 3.84-3.91 (m, 1H), 3.81 (s, 3H), 3.80 (s, 3H), 3.58-3.66 (m, 2H), 3.31-3.54 (m, 5H), 1.56 (s, 9H), 0.96 (s, 9H), 0.14 (s, 3H), 0.07 (s, 3H).

Provenance & Evidence