Boron tribromide → Methyl (5-hydroxy-2,3-dihydro-1H-inden-1-yl)acetate

Participants

Reaction Steps

A 1.0 M solution of boron tribromide in dichloromethane (22.7 mL, 22.7 mmol) was added to an ice-cold solution of methyl (R/S)-(5-methoxy-indan-1-yl)acetate (2.00 g, 9.08 mmol, from Step B) in dichloromethane (15 mL). The cooling bath was removed and the reaction mixture stirred at ambient temperature. After 1 hr, the reaction mixture was slowly transferred to an ice-cold solution of methanol (50 mL). Methanol was removed in vacuo, and the residue was partitioned between EtOAc and sat. NaH2PO4. The organic layer was washed with H2O, brine, and dried over MgSO4. The mixture was filtered, concentrated in vacuo and purified by flash chromatography (15, 20% EtOAc/hexanes) on SiO2 to afford 1.74 g of the title compound: 1H NMR (CDCl3) δ 1.72-1.79 (m, 1H), 2.35-2.42 (m, 1H), 2.46 (dd, 1H, J=8.5, 15.3 Hz), 2.76 (dd, 1H, J=5.9, 15.3 Hz), 2.80-2.92 (m, 2H), 3.50-3.55 (m, 1H), 3.75 (s, 3H), 5.63-5.86 (brs, 1H), 6.67 (dd, 1H, J=2.4, 8.1 Hz), 6.74 (d, 1H, J=2.0 Hz), 7.01 (d, 1H, J=8.3 Hz).

Provenance & Evidence