Tetrabutylammonium Fluoride → HCID 69084598, compound

Participants

Reaction Steps

A solution of 147 (15 g, 21 mmol) in THF (100 mL) was treated with TBAF (8.4 g, 32 mmol) for 3 hours at room temperature. The reaction was quenched with water (150 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layer was washed with brine (2×50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by flash column chromatography with 10%-30% ethyl acetate in petroleum ether to afford 148 as a light yellow syrup (11.3 g, 90%). (ES, m/z): [M+H]+ 601.0; 1H NMR (300 MHz, CDCl3) δ 7.36-7.33 (m, 2H), 7.21-7.19 (m, 2H), 6.91-6.82 (m, 4H), 6.09 (d, J=6.6 Hz, 1H), 5.92-5.80 (m, 1H), 5.19-5.00 (m, 2H), 4.70-4.58 (m, 2H), 4.55-4.36 (m, 4H), 4.32-4.24 (m, 2H), 3.82 (s, 3H), 3.83 (s, 3H), 3.75-3.68 (m, 2H), 3.64-3.52 (m, 2H), 1.56 (s, 9H).

Provenance & Evidence