Methyl iodide → HCID 22861097, compound

Participants

Reaction Steps

A solution of cis-4b,5,9b,10-tetrahydro-8-isopropylindeno[1,2-b]indole (1.75 g, 7.0 mmol) in THF (10 cm3), was added to a suspension of sodium hydride (200 mg, 1.2 equivalents) in THF (7 cm3), at 0° C. The reaction was stirred for two hours and iodomethane (0.53 cm3, 1.2 equivalents) was added. The reaction was stirred overnight, and then quenched with a saturated solution of ammonium chloride. The organic phase was separated, and the aqueous phase extracted with diethyl ether. The combined organic phases were dried (Na2SO4), and solvent removed in vacuo to yield the title compound as a colourless gum which was purified by bulb to bulb distillation. Yield: 1.0 g (54%). B.p. 200° C. at 0.4 mmHg. 1H NMR (CDCl3) δ: 1.22 (6H, d,), 2.81 (1H, septet,), 2.94 (3H, s,), 3.09 (1H, dd,), 3.43 (1H, dd,), 4.15 (1H, ddd,), 4.90 (1H, d,), 6.32 (1H, d,), 6.93 (1H, dd,), 7.02 (1H, br,), 7.1-7.5 (4H, m,).

Provenance & Evidence