Ethanol → ethyl {1-benzyl-5-phenyl-1H-indol-3-yl}(oxo)acetate

Participants

Reaction Steps

Ethyl {1-benzyl-5-phenyl-1H-indol-3-yl}(oxo)acetate was prepared from 1-benzyl-5-phenyl-1H-indole (0.846 g, 2.99 mmol), oxalyl chloride (0.78 mL, 9.0 mmol), and ethanol (2 mL), following the procedure described in Step 3 of Example 1. Purification by flash chromatography (Biotage apparatus) using 5-7.5% ethyl acetate in hexane as an eluant yielded the title compound as a light yellow solid (0.754 g, 66%), mp: 116-117° C. Mass spectrum (+ES, [M+H]+) m/z 384; 1HNMR (500 MHz, DMSO-d6): δ 8.7 (s, 1H), 8.4 (d, 1H, J=0.92 Hz), 7.6-7.7 (m, 3H), 7.55-7.6 (m, 1H), 7.45 (t, 2H, J=7.7 Hz), 7.3-7.4 (m, 6H), 5.65 (s, 2H), 4.35 (q, 2H, J=7.1 Hz), and 1.35 ppm (t, 3H, J=7.1 Hz). Elemental Analysis for C25H21NO3: Calculated: C, 78.31; H, 5.52; N, 3.65. Found: C, 78.15; H, 5.63; N, 3.51.

Provenance & Evidence