Sodium hydride → HCID 178447093, compound

Participants

Reaction Conditions

Reaction Steps

The above product was isolated as a side product in the following reaction: To a solution of benzo[d][1,3]dioxol-5-amine (0.447 mmol) in N,N-dimethylformamide (2 mL) was added NaH (0.447 mmol) at room temperature and after stirring for 15 min 3,3-dimethyl-5-(2-(1-trityl-1H-imidazol-4-yl)phenoxy)pentyl 4-methylbenzenesulfonate (0.223 mmol) was added as a solution in N,N-dimethylformamide (1 mL). The reaction was stirred at 80° C. overnite. After cooling to room temperature, the reaction mixture was diluted with methanol (2 mL) and acetic acid (2 mL). The reaction was heated to 80° C. for 3 h, after cooling to room temperature, the reaction mixture was partitioned between dichloromethane (30 mL) and 20% sodium bicarbonate solution (10 mL), the organic layer was separated and the aqueous phase extracted with dichloromethane (3×25 mL). The combined organic extract was dried (Na2SO4) and concentrated to afford the crude. Yield 7%. 1H NMR: 1.10 (s, 6H), 1.24 (s, 1H), 1.62 (t, 2H, J=7.32 Hz), 1.89 (t, 2H, J=7.24 Hz), 3.75 (t, 2H, J=7.44 Hz), 4.16 (t, 2H, J=7.24 Hz), 6.97 (d, 1H, J=8.52 Hz), 7.01 (d, 1H, J=7.52 Hz), 7.21 (m, 1H), 7.51 (s, 1H), 7.69 (s, 1H), 7.78 (d, 1H, J=7.60 Hz).

Provenance & Evidence