Ethyl bromoacetate → HCID 86623626, compound

Participants

Reaction Steps

To a mixture of activated Zn dust (1.46 g, 22.3 mmol) in THF (10 mL), a solution of 5-methoxy-6-methylindanone (2.62 g, 14.8 mmol, from Step B) from and ethyl bromoacetate (2.14 mL, 19.3 mmol) in THF (15 mL) were added dropwise via cannula. The reaction was heated to reflux for 45 min and cooled to ambient temperature. The reaction was quenched into 2 N HCl and extracted with EtOAc. The organic layer was washed with H2O, brine, dried over MgSO4, and filtered. Solvents were removed in vacuo, and the residue was purified by flash chromatography (5% EtOAc/hexanes) on SiO2 to afford 2.64 g that was recrystallized from hexanes to afford 2.02 g of the title compound as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.35 (t, 3H, J=7.2 Hz), 2.24 (s, 3H), 3.04-3.06 (m, 2H), 3.29-3.31 (m, 2H), 3.88 (s, 3H), 4.23, (q, 2H, J=7.1 Hz), 6.16 (t, 1H, J=2.4 Hz), 6.79 (d, 1H, J=8.8 Hz), 7.38 (d, 1H, J=8.5 Hz).

Provenance & Evidence