tert-Butyl acetate → HCID 91464311, compound

Participants

Reaction Steps

To a cooled (−78° C.) solution of LHMDS (36.5 mL, 1.0 M in THF, 36.5 mmol) was added tert-butyl acetate (4.92 mL, 36.5 mmol), dropwise. After 30 min, a solution of the title compound of Example 14 Step A (4.50 g, 12.2 mmol) in THF (12 mL) was added, and the mixture was held at −78° C. for 30 min, then was placed in a 0° C. bath. After 1.5 h, the reaction mixture was poured into sat. aq. NH4Cl and extracted twice with ethyl acetate. The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 20%, then 20 to 100% EtOAc in hexanes) afforded the title compound: LCMS B, tr=3.11 min, m/z 462.2 [M+Na]+; 1H NMR (500 MHz, CDCl3) δ 7.69 (d, J=2.0 Hz, 1H), 7.31-7.24 (m, 5H), 6.97 (d, J=8.5 Hz, 2H), 5.80 (s, 2H), 3.85 (s, 2H), 1.39 (s, 9H), 1.25 (s, 9H).

Provenance & Evidence