Cyclohexene oxide → HCID 16738222, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1e (23.5 g, no more than 182 mmol), cyclohexene oxide (23 mL, 220 mmol) and water (8 mL) was heated at 80° C. for 2 h. The reaction mixture was then partitioned between 40% NaOH aq (60 mL) and Et2O (120 mL). The basic aqueous layer was extracted twice more with Et2O (2×120 mL). The combined organic extracts were dried and concentrated in vacuo. The residue was then heated under high vacuum at 50° C. for 1 h with stirring (to remove the excess of cyclohexene oxide) to yield 32.8 g of 2e (79% yield); as illustrated in FIG. 2. Rf 0.33 (EtOAc-iPrNrH2, 98:2,v/v); 13C NMR (50 MHz, APT, CDCl3) δ 115.5 (+), 70.0 (−), 65.0 (−), 64.5 (+), 57.0 (+), 46.5 (+), 36.0 (+), 33.5 (+), 25.0 (+), 24.0 (+), 21.5 (+); IR (film) 3457 cm−1.

Provenance & Evidence