Water → HCID 178521363, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product of step b (2.10 g, 4.55 mmol) in acetic acid (20 ml) and THF (20 ml) was added water (2 ml). The mixture was cooled to 5° C. and an aqueous solution (3 ml) of sodium nitrite (0.41 g, 5.92 mmol) was added dropwise while maintaining the temperature below 10° C. Upon completion of the addition, the reaction mixture was allowed to warm to room temperature and stirred for 1 h. The THF and acetic acid were removed in vacuo and the solution was partitioned between water (100 ml) and ethyl acetate (100 ml). 1M NaOH was added until pH 8 was reached, the layers were separated, and the aqueous layer was washed with ethyl acetate (20 ml). The combined organic layers were washed with brine (100 ml), dried (MgSO4) and the solvent was evaporated to yield a yellow oil (2.13 g, 96%). The crude product was purified by flash column chromatography (silica, DCM/ethyl acetate 95:5) to afford a yellow foam (1.29 g, 58%). 1H NMR (300 MHz, CDCl3) 11.04 (1H, br s), 8.23 (1H, s), 7.94 (1H, d), 7.86 (1H, d), 7.50-7.36 (6H, m), 5.39 (2H, s), 4.82 (2H, s), 2.20 (3H, br s), 1.81 (6H, s), 1.65 (6H, m).

Provenance & Evidence