tert-Butyl acetate → HCID 91226750, compound

Participants

Reaction Steps

To a cooled (−78° C.) solution of LHMDS (13 mL, 1.0 M in THF, 13.0 mmol) in THF (13 mL) was added tert-butyl acetate (1.76 mL, 13.0 mmol), dropwise. After 30 min, a solution of the title compound of Example 9 Step A (1.60 g, 4.36 mmol) in THF (4 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. NaHCO3 and extracted twice with ethyl acetate. The combined organic phases were concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 30%, then 30 to 100% hexanes in ethyl acetate) afforded the title compound: LCMS C, tr=2.99 min, m/z 382.1 [M−tBu+H]+; 1H NMR (500 MHz, CDCl3) δ 7.74 (d, J=2.0 Hz, 1H), 7.72 (d, J=8.0 Hz, 1H), 7.64 (t, J=8.0 Hz, 1H), 7.56 (s, 1H), 7.50 (d, J=8.0 Hz, 1H), 7.38 (s, 1H), 7.29 (dd, J=9.0, 2.0 Hz, 1H), 7.01 (d, J=9.0 Hz, 1H), 3.83 (s, 2H), 1.44 (s, 9H).

Provenance & Evidence