Water → HCID 57124282, compound

Participants

Reaction Steps

5,10-Dihydro-2-methoxy-1,3-dimethyl-8-isopropylindeno[1,2-b]indole (1.68 g, 5.5 mmol) was dissolved in trifluoroacetic acid (10 cm3) and stirred vigorously. Triethylsilane (1 cm3, 1.1 eq) was added, and stirring continued for 4 hours. The reaction was poured into water, stirred for 15 minutes, and neutralised with 2M NaOH. All organic material was extracted into ethyl acetate, washed with water and dried (Na2SO4 ). After removal of solvent, the solid material was recrystallised from 60°-80° petroleum ether as white needles. Yield: 1.18 g, 70% .M.p. 106° C. 1H NMR (CDCl3) δ: 7.05 (1H, s), 6.97 (1H, s), 6.88 (1H, dd, J=8.6 Hz), 6.55 (1H, d, J=8.1 Hz), 5.19 (1H, d, J=8.4 Hz), 4.18 (1H, ddd), 3.8 (1 H, br), 3.64 (3H, s), 3.36 (1H, dd, J=16.5, 8.3 Hz), 3.07 (1H, d(br) J=16.5 Hz), 2.81 (1H, septet, J=7.0 Hz), 2.25 (3H, s), 2.15 (3H, s), 1.20 (6H, d, J=7.0 Hz).

Provenance & Evidence