Ethyl orthoformate → HCID 24994043, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of the product of Step A (61 mg, 0.11 mmol) in 5.0 mL of triethyl orthoformate was added one drop of BF3.Et2O. After stirring at 110° C. for 1 h, the reaction mixture was diluted with EtOAc (20 mL) and washed with saturated aq NaHCO3 (2×50 mL) and brine (50 mL). The organic layer was separated, dried over MgSO4, and concentrated. Chromatography on a Biotage 40+S cartridge using 7:13 v/v EtOAc/hexanes as the eluant afforded the title compound: 1H NMR δ 1.27 (s, 9H), 1.48 (s, 3H), 1.56 (s, 3H), 1.84 (t, J=11.4, 1H), 2.27 (dd, J=6.2, 13.0, 1H), 5.50 (m, 1H), 5.84 (br. s, 1H), 7.01 (d, J=8.3, 2H), 7.16 (d, J=8.2, 2H), 7.45 (m, 1H), 7.58 (s, 1H), 7.96-8.04 (m, 2H), 8.77 (s, 1H).

Provenance & Evidence