m-Chloroperbenzoic acid → HCID 11447722, compound

Participants

Reaction Conditions

Reaction Steps

At 0° C., a solution of 4,7,7,9-tetramethyl-1-methylenespiro[4.5]decan-2-one (1.43 g, 6.49 mmol), in CH2Cl2 (10 mL) was added dropwise within 45 min. to a stirred solution of 70% 3-chloroperbenzoic acid (1.76 g, 7.14 mmol) in CH2Cl2 (20 mL). After further stirring at 0° C. for 1 h, the cooling bath was removed, and the reaction mixture stirred for 3 d, with an additional portion of 70% 3-chloroperbenzoic acid (1.76 g, 7.14 mmol) being added after the first and second day. The insoluble material was removed by vacuum filtration and washed with CH2Cl2. The combined organic solutions were washed with 20% aq. NaHSO3, halfconc. NaHCO3, and water (50 mL), the aqueous washings again extracted with CH2Cl2 (50 mL). The combined organic extracts were dried (Na2SO4) and concentrated in a rotary evaporator. The resulting residue was purified by silica-gel FC (pentane/Et2O, 19:1, Rf=0.11) to provide 6,6,8,10-tetramethyl-1-oxadispiro[2.0.5.3]dodecan-12-one (930 mg, 61%).

Provenance & Evidence