Phenylacetone → HCID 67126101, compound

Participants

Reaction Steps

To a solution of 1-chloro-4-ethynylbenzene (3C) (1.75 mL, 12.81 mmol) in THF (40 mL) at 0° C. was added n-butyllithium (2.5 M in hexanes, 5.13 mL, 12.81 mmol) and stirred for 1 h. A solution of 1-phenylpropan-2-one (3B) (1.38 g, 10.25 mmol) in THF (5 mL) was added and the reaction mixture was warmed to room temperature overnight. The reaction mixture was quenched with saturated NH4Cl solution and extracted with diethyl ether (2×). The combined organic layer was dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes) to give 3D as a yellow oil (2.29 g). 1H-NMR: 300 MHz, (CDCl3) δ 7.35-7.20 (m, 9H), 3.0 (AB quart, J=13.2, 9.9 Hz, 2H), 1.59 (s, 3 H).

Provenance & Evidence