Acetic Anhydride → HCID 56986525, compound

Participants

Reaction Steps

4b,5,9b,10-Tetrahydro-4b,8,9b-trimethylindeno[1,2-b]indole (0.25 g, 1.00 mmol) was dissolved in acetic anhydride (1 cm3) and stirred at room temperature for 16 hours. The reaction mixture was poured into saturated sodium bicarbonate solution (25 cm3) and stirred for 1/2 hour. The mixture was extracted with diethyl ether (3×10 cm3) and the combined organic extracts were washed with brine, dried (Na2SO4) and evaporated. The crude material was purified by flash chromatography on silica gel eluting with 4% ethyl acetate/60°-80° petrol to yield a pale yellow gum. Yield: 0.15 g, 53%. 1H NMR (CDCl3) δ: 7.84 (1H, s), 6.90-7.23 (6H, m), 3.26 (1H, d, J=15.9 Hz), 2.96 (1H, d, J =15.9 Hz), 2.40 (3H, s), 2.31 (3H, s), 1.77 (3H, s), 1.32 (3H, s).

Provenance & Evidence