2-Bromoethanol → HCID 18522132, compound

Participants

Reaction Conditions

Reaction Steps

Potassium carbonate (0.2 g) was added to a stirred solution of methyl N-benzyl-4-hydroxyindole-2-carboxylate (0.2 g) and 2-Bromoethanol (98 mg) in DMF (15 ml). The reaction was then stirred for 16 hours at 80° C. under an atmosphere of argon. The reaction mixture was concentrated in vacuo and the residue partitioned between ethyl acetate and water. Combined organic extracts were washed with water, dried (MgSO4), concentrated in vacuo and the residue purified by column chromatography using 70% ethyl acetate: isohexane as eluent to give the product as a colourless crystalline solid. (64 mg, 27%); NMR d (CD3SOCD3) 3.74-3.82 (m, 5H), 4.10 (m, 2H), 4.88 (m, 1H), 5.80 (s, 2H), 6.58 (m, 1H), 6.98 (d, 2H), 7.09 (m, 1H), 7.14-7.27 (m, 4H), 7.38 (m, 1H); M/z (+) 326 (MH+).

Provenance & Evidence