(+/-)-3-Methyl-1-tribromomethyl-2-butenyl diazoacetate → 4-Tribromomethyl-6,6-dimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane

HRID 127035

반응식

HRID 127035 반응식
[N+](=[CH:3][C:4]([O:6][CH:7]([C:12]([Br:15])([Br:14])[Br:13])[CH:8]=[C:9]([CH3:11])[CH3:10])=[O:5])=[N-]>C1(C)C=CC=CC=1.CC(CC(C)=O)=O.CC(CC(C)=O)=O.[Cu]>[Br:13][C:12]([Br:15])([Br:14])[CH:7]1[CH:8]2[CH:3]([C:9]2([CH3:11])[CH3:10])[C:4](=[O:5])[O:6]1

참가 물질

4

반응물 1

HCID 53875604(+/-)-3-Methyl-1-tribromomethyl-2-butenyl diazoacetate

생성물 1

HCID 125252254-Tribromomethyl-6,6-dimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane수율 28%

시약·촉매·용매 2

HCID 45052134Bis(pentane-2,4-dione-kappa~2~O~2~,O~4~)copper촉매HCID 1140Toluene용매2회

실험 절차

To a refluxing solution of cupric acetylacetonate (0.005 g, 0.019 mmole) in 40 ml of toluene was added dropwise over a period of 2.5 hours under an atmosphere of argon gas a solution of (±)-3-methyl-1-tribromomethyl-2-butenyl diazoacetate (0.203 g, 0.005 ml) in 10 ml of toluene. The mixture was then heated under reflux for one hour. After cooling, the reaction mixture was washed successively with two portions of 1 N aqueous hydrochloric acid, once with saturated aqueous sodium bicarbonate, and twice with saturated aqueous sodium chloride. After drying over magnesium sulfate, the solution was evaporated to give a yellow oil as the residue. The residue was purified by column chromatography on a silica gel column using 9/1 n-hexane/ethyl acetate as the eluent, yielding (±)-4-tribromomethyl-6,6-dimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane (0.053 g, yield 28%); mp 101°-103° after recrystallization from n-hexane.

후처리

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for one hour
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed successively with two portions of 1 N aqueous hydrochloric acid, once with saturated aqueous sodium bicarbonate
  5. dry with materialAfter drying over magnesium sulfate
  6. customthe solution was evaporated
  7. customto give a yellow oil as the residue
  8. customThe residue was purified by column chromatography on a silica gel column

출처 및 근거

ORD 기록
ord-addd5f4f14574345a8697c96a03c20a8
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04254282

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