반응 #74891

반응 방정식

(1S,2S,5R)-2-methyl-6-oxabicyclo[3.1.0]hexan-3-one

sodium bicarbonate

m-chloroperbenzoic acid

→

(1S,2S,6R)-2-methyl-3,7-dioxabicyclo[4.1.0]heptan-4-one

용매

methylene chloride

반응 조건

후처리

1. 1
   여과filtered through Celite Filter-Aid
2. 2
   기타The filtrate was evaporated to dryness under reduced pressure
3. 3
   기타the residue was triturated with 40 ml of methylene chloride and insolubles
4. 4
   기타were removed by filtration
5. 5
   세척The filtrate was washed twice with a saturated aqueous solution of sodium bicarbonate
6. 6
   건조dried over magnesium sulfate
7. 7
   기타evaporated to dryness under educed pressure
8. 8
   온도Heating at 70° (0.1 mm)
9. 9
   기타removed 0.95 g of volatile material
10. 10
    기타The oily residue slowly crystallized

실험 절차

To a solution of 5.6 g (50 mmol) of (1S,2S,5R)-2-methyl-6-oxabicyclo[3.1.0]hexan-3-one (4) in 400 ml of anhydrous methylene chloride was added 15 g of sodium bicarbonate and 12.9 g (64 mmol) of 85% m-chloroperbenzoic acid. The suspension was stirred at room temperature for 72 hr and filtered through Celite Filter-Aid. The filtrate was evaporated to dryness under reduced pressure, the residue was triturated with 40 ml of methylene chloride and insolubles were removed by filtration. The filtrate was washed twice with a saturated aqueous solution of sodium bicarbonate, dried over magnesium sulfate and evaporated to dryness under educed pressure. Heating at 70° (0.1 mm) removed 0.95 g of volatile material. The oily residue slowly crystallized on standing to give (1S,2S,6R)-2-methyl-3,7-dioxabicyclo[4.1.0]heptan-4-one: mp 51°-52°. Recrystallization from 12 ml of ether yielded end product: mp 51° -52°. Several recrystallizations from ether gave analytically pure (1S,2S,6R)-2-methyl-3,7-dioxabicyclo-[4.1.0]heptan-4-one: mp 52.5°-53.5°; [α]25D +147.26 (c 0.995, MeOH).

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