Sodium borohydride → HCID 58858087, compound

Participants

Reaction Steps

To a mixture of 1-(2-methoxy-4-nitrophenoxy)propan-2-one (300 mg, 1.33 mmol) in 1.3 mL of MeOH and 1.3 mL of H2O at rt was added a solution of NaBH4 (53 mg, 1.40 mmol) in 0.5 mL of H2O dropwise over 5 min. The suspension was stirred at rt for 1 h and diluted with 0.2 mL of HOAc followed by 2 mL of H2O. The precipitate was filtered, washed with H2O and dried under vacuum to afford the title compound (270 mg) as a yellow solid. 1H NMR (CDCl3) δ 1.28 (d, J=6.05 Hz, 3H), 2.68, (s, 1H), 3.87-3.92 (m, 4H), 4.03-4.05 (m, 1H), 4.23-4.29 (m, 1H), 6.89 (d, J=9.35 Hz, 1H), 7.72 (d, J=2.20 Hz, 1H), 7.86 (dd, J=8.80 Hz, 2.75 Hz, 1H); 13C NMR (CDCl3) δ 18.66, 56.19, 65.90, 74.84, 106.73, 111.66, 117.60, 141.79, 149.21, 153.62; HPLC (Method # 1) 2.29 min retention time, (100%); LCMS (ES): m/z 228 [M+H]+.

Provenance & Evidence