Tetrabutylammonium Fluoride → HCID 69082482, compound

Participants

Reaction Steps

A solution of 133 (7.5 g, 9.3 mmol) in THF (30 mL) was treated with TBAF (4.9 g, 18.6 mmol) for 3 hours at room temperature. The reaction was quenched with water (100 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine (2×30 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluted with 3%-10% ethyl acetate in petroleum ether to afford 134 as a light yellow syrup (5.8 g, 90%). (ES, m/z) [M+H]+ 695.0; 1H NMR (300 MHz, CDCl3) δ 7.21-7.36 (m, 9H), 6.80-6.85 (m, 4H), 6.09 (d, J=6.3 Hz, 1H), 4.50-4.55 (m, 4H), 4.49 (s, 2H), 4.31-4.33 (m, 1H), 4.05-4.06 (m, 1H), 3.84-3.91 (m, 1H), 3.82 (s, 3H), 3.83 (s, 3H), 3.56-3.67 (m, 2H), 3.30-3.53 (m, 5H), 1.56 (s, 9H).

Provenance & Evidence