Ethanol → HCID 67076937, compound

Participants

Reaction Conditions

Reaction Steps

Add 0.45 mL of toluene, 0.1 mL of absolute ethanol, and vinylboronic acid dibutyl ester (0.030 mL, 0.136 mmol) to a 4 mL vial containing preparation 16 (30 mg, 0.062 mmol) and Pd(PPh3)4 (7 mg, 0.0061 mmol). Bubble nitrogen through the solution for 5 min, seal tightly, and warm to 80° C. with stirring overnight. Dilute the solution with EtOAc and wash with brine. Back extract the aqueous solution with EtOAc. Wash the combined organic solutions with brine, dry over Na2SO4, filter, and concentrate. Adsorb the material to 500 mg of silica gel and purify by silica gel flash chromatography (4 g, 0-20% A/B, A=EtOAc, B=10% CH2Cl2 in hexanes) to afford 12 mg (0.028 mmol, 45%) of preparation 18. 1H NMR (400 MHz, CDCl3) δ 7.38-7.33 (m, 2H), 7.14-7.05 (m, 4H), 6.74 (d, 1H, J=2.6 Hz), 5.77 (dd, 1H, J=1.3, 18.1 Hz), 5.28 (dd, 1H, J=1.3, 12.3 Hz), 5.20 (s, 2H), 5.15 (d, 1H, J=10.1 Hz), 5.13 (d, 1H, J=9.7 Hz), 5.02 (bs, 1H), 3.67 (dt, 1H, J=3.1, 11.0 Hz), 3.50 (s, 1H), 2.89 (m, 1H), 2.74 (m, 1H), 2.30 (m, 1H), 2.17 (m, 1H), 1.86 (m, 1H).

Provenance & Evidence