Borane → HCID 18182599, compound

Participants

Reaction Steps

A solution of 5-bromo-3-(carboxymethyl)-2,3-dihydro-benzofuran (reference example 15, 1.86 g , 7.68 mmol) in THF (21 mL) is cooled to 0° C. then a solution of borane in THF (7.7 mL, 1 M). On complete addition the cold bath is removed and stirring continued for 12 h. The reaction is quenched with aq. HCl (2M) diluted with ethyl acetate washed with sat. NaHCO3 solution then brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (30% ethyl acetate in hexanes) to give the title compound (1.1 g) as an oil. 1H NMR (CDCl3) d 1.55 (bs, 1H), 1.88 (m, 1H), 2.03 (m, 1H), 3.61 (m, 1H), 3.75 (t, J=6 Hz, 2H), 4.29 (dd, J=8, 7 Hz, 1H), 4.68 (t, J=8 Hz, 1H), 6.68 (d, J=8 Hz, 1H), 7.22 (dd, J=8, 1 Hz, 1H), 7.28 (d, J=1 Hz, 1H). MS m/z242/244 Br pattern (M+).

Provenance & Evidence