Ethyl Acetate → Methyl 4-[5-(1-hydroxyallyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate

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Reaction Steps

Vinyl magnesium bromide (3.05 ml of a 1 molar solution in tetrahydrofuran) was added dropwise to a stirred solution of methyl 4-(5-formyl-1-propylindol-3-ylmethyl)-3-methoxybenzoate (1 g, prepared as described in Example 61, part a) in dry tetrahydrofuran (50 ml), at 0° under an atmosphere of nitrogen. The mixture was stirred at 0° for 15 min, and then poured rapidly into a stirred mixture of saturated aqueous ammonium chloride (100 ml) and ethyl acetate (150 ml). The aqueous layer was further extracted with ethyl acetate (75 ml), and the combined organic layers washed (water (twice), brine), dried (MgSO4) and evaporated to give methyl 4-[5-(1-hydroxyallyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (1.03 g, 95%) as a yellow oil; partial NMR (250 MHz, DMSO-d6): 0.80(t, 3H, CH2CH3), 1.75(m, 2H, CH2CH3), 3.83(s, 3H, OCH3), 3.91(s, 3H, OCH3), 4.0(m, 4H, ArCH2Ar', NCH2), 5.0-5.3(m, 4H, H2C=CH, CH(OH)), 5.9(m, 1H, CH=CH2).

Provenance & Evidence