2-Heptanone → 3-(Chloromethyl)cyclohexanone

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared following the procedure described in (N. Di Bello et al., Synthesis, 1978, 227. To a solution of bicycle[4.1.0]heptan-2-one (13.8 g, 125 mmol) in acetonitrile (300 mL) was added pyridine hydrochloride (43.3 g, 375 mmol) which had been triturated with Et2O and dried under high vacuum. The solution was stirred under N2 at 82° C., overnight. The reaction mixture was partially concentrated, poured into brine (200 mL) and extracted with Et2O (4×100 mL). The ether extracts were combined, washed with brine (100 mL), dried and concentrated. The residual oil was purified on a Biotage flash chromatography system (15% ethyl acetate in hexanes) to yield the title compound (13.4 g, 91 mmol, 73.1% yield) as an oil. LCMS: 147.09 (M+H), 149.10 (M+3, 30% rel. intensity). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1.51-1.60 (m, 1 H) 1.62-1.74 (m, 1 H) 1.95-2.02 (m, 1 H) 2.06-2.13 (m, J=13.47, 9.80, 3.62, 3.62 Hz, 1 H) 2.13-2.20 (m, 1 H) 2.20-2.31 (m, 2 H) 2.35-2.43 (m, 1 H) 2.45-2.51 (m, 1 H) 3.45-3.55 (m, 2 H). 13C NMR (126 MHz, CHLOROFORM-d) δ ppm 24.63, 28.75, 40.85, 41.15, 45.39, 210.25.

Provenance & Evidence