Potassium Iodide → (4-Iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate

HRID 132990

반응식

HRID 132990 반응식
[C:1]([O:4][CH2:5][C:6]1[C:16]2[CH2:15][CH2:14][C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[C:11](=[O:21])[C:10]=2[CH:9]=[CH:8][CH:7]=1)(=[O:3])[CH3:2].FC(F)(F)C([O-])=O.[Tl+].[I-:30].[K+].C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O.O.C(OCC)(=O)C>[C:1]([O:4][CH2:5][C:6]1[C:16]2[CH2:15][CH2:14][C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[C:11](=[O:21])[C:10]=2[C:9]([I:30])=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

참가 물질

8

반응물 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 21902506Thallium(1+);2,2,2-trifluoroacetateHCID 58646841(5-Oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate

생성물 1

HCID 12150904(4-Iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate

시약·촉매·용매 3

HCID 962Water용매HCID 6422Trifluoroacetic acid용매HCID 8857Ethyl Acetate용매

실험 절차

4.4 g of (5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-1-yl)methyl acetate prepared in Example 1-f was dissolved in 30 ml of trifluoroacetic acid, and 5.0 g of thallium trifluoroacetate was added at room temperature in an atmosphere of nitrogen gas. The mixture was stirred at room temperature for 4 hours, followed by stirring at 50° C. for 2 hours. After the starting material disappeared, 3 ml of an aqueous solution of 1.5 g of potassium iodide was added to the reaction mixture and the mixture was stirred at room temperature for 0.5 hour. To the reaction mixture were added ethyl acetate and water, and the mixture was neutralized with sodium hydrogencarbonate and filtered through Celite. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:20), to give 4.1 g of a 3:1 mixture of the title compounds as a colorless oil.

후처리

  1. stirringby stirring at 50° C. for 2 hours
  2. stirringthe mixture was stirred at room temperature for 0.5 hour
  3. filtrationfiltered through Celite
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified
  8. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:20)
  9. customto give

출처 및 근거

ORD 기록
ord-beb1bafe3a1c4769af44e738bbebdf18
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390797B2

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