Sodium Phosphate, Dibasic → HCID 57004359, compound

Participants

Reaction Steps

(3S, 4S)-(-)-6-Butoxy-2,2-dimethyl-3,4-epoxychroman At 0° C., 76 ml (42 mmol) of a 0.55 M sodium hypochlorite solution which had been adjusted to pH 11.3 using disodium hydrogen phosphate were added to a solution of 4.6 g (20 mmol) of 6-butoxy-2,2-dimethyl-2H-chromen (Example 5b) and 0.5 g (0.8 mmol) of (S,S)-(+)-N,N'-bis-(3,5-di-tert-butylsalicylidene)-1,2-diaminocyclohexanemanganese(III) chloride (Jacobsen's catalyst) in 20 ml of methylene chloride. The reaction mixture was stirred vigorously for 3 h and the organic phase was then separated off and the aqueous phase was extracted twice with methylene chloride. Silica gel chromatography of the crude product using cyclohexane/EA 9:1 gave 1.6 g of (3S, 4S)-(-)-6-butoxy-2,2-dimethyl-3,4-epoxychroman; optical rotation -14.9° (c=0.6; methanol).

Provenance & Evidence