Methanol → HCID 68850203, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 5-methoxy-4-methylindane-2-carboxylate (896 mg, 3.82 mmol, from Step B) in dichloromethane (10 mL) cooled to 0° C., BBr3 (1.0 M in CH2Cl2, 19.1 mL, 19.1 mmol) was added dropwise. The reaction mixture was stirred for 30 min at 0° C. and warmed to ambient temperature. After 2 hr, the reaction mixture was slowly transferred to an ice-old solution of methanol (10 mL). The resulting solution was warmed to ambient temperature, concentrated in vacuo, and azeotroped with methanol (2×5 mL). The residue was partitioned between EtOAc (15 mL) and sat. NaH2PO4 (5 mL). The layers were separated, and the EtOAc layer was washed with H2O (1×5 mL), brine (1×5 mL) and dried (MgSO4). The mixture was filtered, concentrated in vacuo and purified by flash chromatography (10, 20% EtOAc/hexanes) on SiO2 to afford 560 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 2.15 (s, 3H), 3.13-3.22 (m, 4H), 3.35 (quintet, 1H, J=8.6 Hz), 3.73, (s, 3H), 4.66 (s, 1H), 6.61 (d, 1H, J=8.1 Hz), 6.89 (d, 1H, J=8.1 Hz).

Provenance & Evidence