Tetrahydrofuran → HCID 66583106, compound

Participants

Reaction Steps

To a solution of ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate (7.89 g, 36.8 mmol) in THF (120 mL) was added LDA (1.5 eq) at −78° C. and stirred for 30 min. Then, benzyl chloromethyl ether (10.7 mL, 92.1 mmol) was added dropwise. The resulting mixture was slowly warmed to rt and stirred overnight. The reaction was quenched with H2O and combined with ammonium choloride. All the volatiles were removed. The residue was diluted with EtOAc, washed with H2O and brine, dried over Na2SO4, and concentrated. The resulting brownish oil was dissolved in CH3CN (150 mL) and a solution of CAN (2.02 g 3.68 mmol) in H2O (150 mL) was added. The resulting mixture was heated at 70° C. for 6 h. Organic solvent was removed under reduced pressure. The aqueous residue was extracted with EtOAc (*3) and the combined organic layers were washed brine, dried over Na2SO4 and concentrated. The crude product was purified by two SiO2 columns (firstly 0-30% EtOAc/Hexanes, then 50-100% DCM/Hexanes, Rf=0.2 in 20% EtOAc) to afford ethyl 1-(benzyloxymethyl)-4-oxocyclohexanecarboxylate as a pale yellow oil (5.72 g). HPLC-MS TR=2.08 min (UV 254 nm, 5 min method); mass calculated for formula C17H22O4 290.2, observed LCMS m/z 291.1 (M+H).

Provenance & Evidence