Cycloheptanol → HCID 63891576, compound

Participants

Reaction Steps

Ethyl 4-chloroacetoacetate (3.00 mL, 22.1 mmol) was added dropwise to an ice-cooled suspension of sodium hydride (60% dispersion in oil, 2.04 g, 51.0 mmol) in DME (20 mL). Immediately cycloheptanol (3.00 mL, 24.9 mmol) was added dropwise and the resultant reaction mixture was allowed to warm slowly to ambient temperature and then stirred at this temperature for 18 h. The reaction mixture was quenched with aqueous 2M hydrochloric acid (100 mL) and extracted with ethyl acetate (100 mL). The aqueous phase was discarded and the organic phase washed with brine (100 mL) and dried (MgSO4). The residue was purified by flash column chromatography (4:1 hexane:ethyl acetate) to afford the tide compound (4.51 g, 84%). 1H NMR (CDCl3) 4.23-4.16 (2H, m), 4.07 (2H, s), 3.55 (2H, s), 3.50-3.47 (1H, m), 1.88-1.87 (2H, m), 1.67-1.53 (8H, m), 1.31-1.26 (5H, m).

Provenance & Evidence