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

HRID 1636447

反応式

HRID 1636447 の反応式
[CH3:1][C:2]1([CH3:12])[C@H:4]([CH:5]=[C:6]([CH3:8])[CH3:7])[C@H:3]1[C:9](Cl)=[O:10].[F:13][C:14]1[C:19]([F:20])=[C:18]([CH3:21])[C:17]([F:22])=[C:16]([F:23])[C:15]=1[CH2:24][OH:25].N1C=CC=CC=1>O1CCCC1>[CH3:1][C:2]1([CH3:12])[C@H:4]([CH:5]=[C:6]([CH3:8])[CH3:7])[C@H:3]1[C:9]([O:25][CH2:24][C:15]1[C:16]([F:23])=[C:17]([F:22])[C:18]([CH3:21])=[C:19]([F:20])[C:14]=1[F:13])=[O:10]

参加物

5

反応物 3

HCID 1049PyridineHCID 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%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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

後処理

  1. temperaturecooling
  2. extractionextracted twice with 100 ml of ethyl acetate
  3. washThe combined ethyl acetate layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=20/1)

出典と根拠

ORDレコード
ord-1b830a87e7ee4673bc868bb63b5d3002
出典データセット
uspto-grants-2000_03
特許番号
US06034128

関連ノート

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