m-Chloroperbenzoic acid → HCID 12817969、化合物

HRID 46613ノート

反応式

HRID 46613 の反応式
[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

参加物

5

反応物 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 56614180HCID 56614180、化合物

生成物 1

HCID 12817969HCID 12817969、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2431c5e714594d9eb17fd86671180588
出典データセット
uspto-grants-1979_11
特許番号
US04174344

反応ノート

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