m-Chloroperbenzoic acid → HCID 12817969, 화합물

HRID 1732552노트

반응식

HRID 1732552 반응식
[CH3:1][C@@H:2]1[C:7](=[O:8])[CH2:6][C@@H:5]2[C@H:3]1[O:4]2.C(=O)(O)[O-:10].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[CH3:1][C@@H:2]1[O:10][C:7](=[O:8])[CH2:6][C@@H:5]2[C@H:3]1[O:4]2

참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 56614180HCID 56614180, 화합물

생성물 1

HCID 12817969HCID 12817969, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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).

후처리

  1. filtrationfiltered through Celite Filter-Aid
  2. customThe filtrate was evaporated to dryness under reduced pressure
  3. customthe residue was triturated with 40 ml of methylene chloride and insolubles
  4. customwere removed by filtration
  5. washThe filtrate was washed twice with a saturated aqueous solution of sodium bicarbonate
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness under educed pressure
  8. temperatureHeating at 70° (0.1 mm)
  9. customremoved 0.95 g of volatile material
  10. customThe oily residue slowly crystallized

출처 및 근거

ORD 기록
ord-c5680152029f4f7892f13d3021cd9276
출처 데이터셋
uspto-grants-1980_12
특허 번호
US04238399

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