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

HRID 132990

反応式

HRID 132990 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6422Trifluoroacetic acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-beb1bafe3a1c4769af44e738bbebdf18
出典データセット
uspto-grants-2008_06
特許番号
US07390797B2

関連ノート

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