Sodium Bicarbonate → HCID 10782713, compound

Participants

Reaction Steps

Added EtOH (0.5 mL) at r.t. to a mixture of 7h (100 mg, 0.3 mmol) and sodium borohydride (12 mg, 0.3 mmol) and then refluxed for 5 minutes. Quenched reaction with 1 m HCl (0.5 mL) and poured into 5% NaHCO3 (15 mL). Aqueous workup (Et2O, MgSO4) followed by concentration in vacuo afforded a yellow oil which was purified by flash chromatography (20 g. 1:1 hexanes/ethyl acetate) to yield 8h (56 mg, 56%) as a crystalline solid: 1H NMR (270 MHz, (CDCl3) d 2.19 (s, 6H), 4.56 (s, 2H), 5.69 (s, 2H), 7.04 (s, 2H), 7.49-7.55 (m, 1H), 7.69-7.72 (m, 2H), 8.15 (d, J=7.9 Hz, 1H); 13C NMR (68 MHz, CDCl3) d 16.1, 64.7, 66.9, 125.4, 127.5, 128.8, 129.3, 130.3, 131.6, 134.1, 138.9, 147.3, 147.69, 152.7.

Provenance & Evidence