Methyl phenylacetate → HCID 68870927, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of freshly prepared lithium diisopropylamine (76.5 mmol) in 500 mL of tetrahydrofuran at 0° C. was added methyl phenylacetate (10.44 g, 69.50 mmol) in 125 mL tetrahydrofuran dropwise over 30 minutes. After stirring at 0° C. for 1 hour the reaction mixture was cooled to −78° C. and treated with 50 mL of hexamethylphosphoric triamide followed by the dropwise addition of bromomethyl cyclobutane (9.37 mL, 83.4 mmol) and LiI (200 mg). The reaction mixture was stirred for 18 hours warming to 25° C. The reaction was quenched over 1 L of water containing 250 mL of sat. NH4Cl and extracted 3× with ethyl acetate. The combined organic layers were washed sequentially with saturated sodium bicarbonate, brine, and dried over MgSO4 yielding the crude product as an oil that was used without further purification. 1H NMR (300 MHz, CDCl3): δ ppm 1.59 (m, 2H) 1.89 (m, 5H) 2.17 (m, 2H) 3.47 (t, J=7.54 Hz, 1H) 3.64 (s, 3H) 7.31 (m, 5H). MS (ESI+) m/z=236 (M+NH4)+.

Provenance & Evidence