Methanol → (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R)-trans-3-formyl-2,2-dimethylcyclopropanecarboxylate

HRID 1976308

反応式

HRID 1976308 の反応式
[CH3:1][C:2]1([CH3:24])[C@H:4]([CH:5]=C(C)C)[C@H:3]1[C:9]([O:11][CH2:12][C:13]1[C:18]([F:19])=[C:17]([F:20])[C:16]([CH3:21])=[C:15]([F:22])[C:14]=1[F:23])=[O:10].CO.O=O.[O:29]=[O+][O-]>CCCCCC.C(OCC)(=O)C.C(OCC)(=O)C>[CH:5]([C@@H:4]1[C@@H:3]([C:9]([O:11][CH2:12][C:13]2[C:18]([F:19])=[C:17]([F:20])[C:16]([CH3:21])=[C:15]([F:22])[C:14]=2[F:23])=[O:10])[C:2]1([CH3:24])[CH3:1])=[O:29]

参加物

7

反応物 4

HCID 887MethanolHCID 977OxygenHCID 24823OzoneHCID 11580987(2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate

生成物 1

HCID 15451879(2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R)-trans-3-formyl-2,2-dimethylcyclopropanecarboxylate収率 82%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

Into a mixture solution of 1.27 g of (2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate, 20 ml of methanol and 20 ml of ethyl acetate, oxygen containing ozone was blown at −78° C. until the color of the solution was changed to blue. Then nitrogen gas was blown into the solution for removing excess ozone, 5 ml of dimethylsulfide was added to the solution and the solution was brought to room temperature. After one day, the reaction solution was concentrated under reduced pressure. To the residue, 20 ml of acetone, 2 ml of water and 0.2 g of p-toluenesulfonic acid monohydrate were added and allowed to stand at room temperature for 2 hours. The reaction solution was poured into water and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a residue, which was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=10/1) to give 0.98 g of (2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1R)-trans-3-formyl-2,2-dimethylcyclopropanecarboxylate (yield 82%). m.p. 43.2° C.

後処理

  1. customwas blown at −78° C. until the color of the solution
  2. customfor removing excess ozone, 5 ml of dimethylsulfide
  3. additionwas added to the solution
  4. customwas brought to room temperature
  5. concentrationthe reaction solution was concentrated under reduced pressure
  6. additionTo the residue, 20 ml of acetone, 2 ml of water and 0.2 g of p-toluenesulfonic acid monohydrate were added
  7. waitto stand at room temperature for 2 hours
  8. additionThe reaction solution was poured into water
  9. extractionextracted with diethyl ether
  10. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customto give a residue, which

出典と根拠

ORDレコード
ord-d89ca1546b74477993af411154607f32
出典データセット
uspto-grants-2001_05
特許番号
US06225495B1

関連ノート

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