Dimethylformamide → HCID 86747564, compound

Participants

Reaction Steps

Sodium hydride, 60% in mineral oil, (134 mg, 3.36 mmol) was added to a solution of 16 (1.15 g, 3.36 mmol) in N,N-dimethylformamide (25 ml) at 0° C. and stirred at rt for 2 h. The reaction was cooled to 0° C. and sodium azide (635 mg, 10.8 mmol) in water (2 ml) was added. After stirring at rt for 1 h, the resultant solution was poured into water (150 ml). The product was extracted with dichloromethane (50 ml), washed several times with water and dried over magnesium sulfate. The solvent was evaporated in vacuo to give the product as a brown oil, 1.0 g (98%), which was used without further purification. 1H NMR (CDCl3): d 1.31 (s, 3 H), 1.48 (s, 3 H), 2.42 (d, J=5.3 Hz, H), 3.72 (d of d, J=7.5 and 5.3 Hz, 1 H), 4.21 (d, J 7.5 Hz, 1 H) and 6,76 (s, 1 H); IR (neat) 3600-3200, 2101, 1663, 1568 and 1470 cm-1 ; MS: m/z 303 MH+).

Provenance & Evidence