Sodium Bicarbonate → HCID 9969649, compound

Participants

Reaction Steps

To a round bottomed flask was added N′-[4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexylidene-4-methylbenzenesulfonohydrazide (100 mg), tetrahydrofuran (5 ml), glacial acetic acid (3 drops) and tetrabutylammonium fluoride hydrate (174 mg), and the resulting solution was stirred at room temperature for 2 hr. Saturated sodium hydrogen carbonate solution (10 ml) was added and stirring was continued for 1 hr. The reaction mixture was partitioned between water (10 ml) and ethyl acetate (20 ml), the layers were separated, and the aqueous phase was extracted with ethyl acetate (2×20 ml). The combined organic phases were washed with brine (10 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via flash chromatography (SiO2, ethyl acetate/petroleum ether, 7:3 v/v) furnished the title compound (62 mg, 100%) as a cream solid. δH ((CD3)2CO): 1.44-1.63 (2H, m), 1.92-2.01 (3H, m), 2.22-2.32 (1H, m), 2.35-2.43 (2H, m), 2.97 (3H, s), 3.09 (1H, tt), 6.28 (H, dd), 6.37 (1H, d), 6.87(1H, d), 7.38 (2H, d), 7.79 (2H, d), 7.96 (1H, s), 8.13 (1H, s), 8.99 (1H, s); m/z (ES+) 375 (M+H)+.

Provenance & Evidence