Water → HCID 15082728, compound

Participants

Reaction Steps

A solution of 5,10-dihydro-8-tert-butylindeno[1,2-b]indole (0.57 g, 2.2 mM) in trifluoroacetic acid (5 cm3) was stirred rapidly, and triethylsilane (0.7 cm3, 2 eq ) added in one portion. The reaction was stirred overnight, poured into water (10 cm3) and neutralised by the addition of sodium hydroxide. The product was extracted into diethyl ether (2×5 cm3), and the combined extracts were washed with water, dried (Na2SO4) and evaporated to yield a pink solid. This was washed with cold petroleum ether (60°-80° C.), and then crystallised from petrol to yield a colourless solid. Yield: 0.47 g, 81% M.p. 103°-105° C.; 1H NMR (CDCl3) δ: 7.4-6.9 (6H, m), 6.58 (1H, d, J=8 Hz), 5.25 (1H, d, J=8.5 Hz), 4.15 (2H, br.m), 3.5 (1H, dd, J=16.0 and 9 Hz), 3.2 (1H, d, J=16 Hz), 1.2 (9H, s).

Provenance & Evidence