Lithium borohydride → HCID 58763424, compound

Participants

Reaction Steps

To a suspension of LiBH4 (0.157 g, 7.2 mmol) in anhydrous DME (50 mL) was added a solution of 1-(3-carboxy-phenyl)-3-ethoxycarbonylmethyl-1H-indole-2-carboxylic acid in DME containing 3% methanol (10 mL). The reaction mixture was heated at reflux for 1 h and then allowed to cool to room temperature. The reaction was quenched with 1 N HCl at 0° C. and extracted with EtOAc. The extract was dried over Na2SO4 and concentrated to afford 0.78 g of 1-(3-carboxy-phenyl)-3-(2-hydroxyethyl)-1H-indole-2-carboxylic acid as a yellow oil (100% crude yield): 1H NMR (CDCl3, 300 MHz) δ 3.28 (t, J=6.87 Hz, 2H), 3.69 (t, J=6.87 Hz, 2H), 7.03 (d, J=8.20 Hz, 1H); 7.18(t, J=7.25 Hz, 1H), 7.28 (t, J=7.25 Hz, 1H), 7.60–7.68 (m, 2H), 7.76–7.81 (m, 2H), 8.02 (d, J=7.06 Hz, 1H).

Provenance & Evidence