Water → HCID 22676835, compound

Participants

Reaction Steps

Ethyl 3-(4-tert-butylphenyl)-1-(3-methoxybenzyl)-5-vinyl-1H-indole-2-carboxylate (Example 129, 2.28 g, 4.9 mmol) was dissolved in anhydrous tetrahydrofuran (25 mL), and osmium tetroxide (2.5 weight % solution in 2-methyl-2-propanol, 1.5 mL, 0.15 mmol) was added. After ten minutes, the reaction mixture was cooled with an ice bath. Sodium periodate (2.10 g, 9.8 mmol) was added followed by a minimum volume of water to dissolve the solids. The reaction was allowed to return to room temperature, and after 30 minutes, the reaction was partitioned between water and diethyl ether. The organic layer was separated, dried over anhydrous magnesium sulfate, and concentrated. The resulting crude oil was passed through a pad of silica gel with 20% ethyl acetate/hexane. The filtrate was concentrated in vacuo without heat to provide the title compound as a brown oil (1.70 g, 75%). The product had: 1H NMR (300 MHz, acetone-d6) 10.01 (s, 1 H), 8.15 (d, 1 H), 7.88 (d, 1 H), 7.75 (d, 1 H), 7.54 (d, 2 H), 7.44 (d, 2 H), 7.21-7.19 (m, 1 H), 6.81-6.79 (m, 1 H), 6.72-6.69 (m, 2 H), 5.92 (s, 2 H), 4.12 (q, 2 H), 3.71 (s, 3 H), 1.39 (s, 9 H), 0.78 (t, 3 H).

Provenance & Evidence