Pyridine → (2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate

HRID 1976307

反応式

HRID 1976307 の反応式
[F:1][C:2]1[C:7]([F:8])=[C:6]([CH3:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[CH2:12][OH:13].N1C=CC=CC=1.O1CCCC1.[CH3:25][C:26]1([CH3:36])[C@H:28]([CH:29]=[C:30]([CH3:32])[CH3:31])[C@H:27]1[C:33](Cl)=[O:34]>CCCCCC.C(OCC)(=O)C>[CH3:25][C:26]1([CH3:36])[C@H:28]([CH:29]=[C:30]([CH3:31])[CH3:32])[C@H:27]1[C:33]([O:13][CH2:12][C:3]1[C:2]([F:1])=[C:7]([F:8])[C:6]([CH3:9])=[C:5]([F:10])[C:4]=1[F:11])=[O:34]

参加物

6

反応物 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 27342094-Methyl-2,3,5,6-tetrafluorobenzyl alcoholHCID 10867076(1R,3R)-2,2-Dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropanecarbonyl chloride

生成物 1

HCID 11580987(2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate収率 87.1%

試薬・触媒・溶媒 1

HCID 21226206Ethyl acetate hexane溶媒

実験手順

To a mixture solution of 1.78 g of (2,3,5,6-tetrafluoro-4-methylphenyl)methanol, 0.87 g of pyridine and 20 ml of tetrahydrofuran, 2.06 g of (1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic chloride was added under ice-cooling and the mixture was stirred for 8 hours at room temperature. The reaction mixture was poured into about 100 ml of ice-water and extracted with each 100 ml of ethyl acetate twice. The combined ethyl acetate was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a crude product, which was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=20/1) to give 2.75 g of (2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (yield 87%).

後処理

  1. temperaturecooling
  2. extractionextracted with each 100 ml of ethyl acetate twice
  3. washThe combined ethyl acetate was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a crude product, which

出典と根拠

ORDレコード
ord-1fb30dc999774aaf95acac4f309849c9
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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