Sodium borohydride → HCID 10737291, compound

Participants

Reaction Steps

Added EtOH (0.5 mL) at r.t. to a mixture of 7e (50 mg, 0.14 mmol) and sodium borohydride (5 mg, 0.14 mmol) and allowed to sit for 1 hour. The reaction was quenched with 1 m HCl (0.5 mL) and poured into 5% NaHCO3 (15 mL). Aqueous workup (Et2O, MgSO4) followed by concentration in vacuo yielded 8e (27 mg, 54%) as a yellow oil: 1H NMR (270 MHz, CDCl3) d 1.56 (d, J=6.2 Hz, 3H), 2.18 (s, 6H), 3.95 (s, 3H), 4.04 (s, 3H), 4.56 (s, 2H), 5.73 (q, J=6.2 Hz, IH), 7.00 (s, 2H), 7.55 (s, 1H), 7.59 (s, 1H); 13C NMR (68 MHz, CDCl3) d 17.6, 23.4, 56.4, 56.5, 65.1, 76.2, 107.5, 109.2, 128.1, 131.0, 135.4, 136.1, 139.0, 147.9, 153.8, 154.6.

Provenance & Evidence