Pyridine → (RS)-3-isopropyl-4-methylidenecyclopenten-2-yl (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate

HRID 1379936ノート

反応式

HRID 1379936 の反応式
C(C1C(=C)CC([OH:10])C=1)(C)C.N1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl:17]/[C:18](/[C:28]([F:31])([F:30])[F:29])=[CH:19]\[C@@H:20]1[C@H:22]([C:23](Cl)=[O:24])[C:21]1([CH3:27])[CH3:26].[C:32]1([CH3:38])[CH:37]=CC=C[CH:33]=1>>[Cl:17]/[C:18](/[C:28]([F:31])([F:30])[F:29])=[CH:19]\[C@@H:20]1[C@H:22]([C:23]([O:10][C:12]2[CH:33]([CH:32]([CH3:38])[CH3:37])[C:15](=[CH2:16])[CH2:14][CH:13]=2)=[O:24])[C:21]1([CH3:27])[CH3:26]

参加物

5

反応物 4

HCID 1049PyridineHCID 1140Toluene2 回HCID 11334477(1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chlorideHCID 22908391(RS)-3-isopropyl-4-methylidenecyclopent-2-en-1-ol

生成物 1

HCID 86749756(RS)-3-isopropyl-4-methylidenecyclopenten-2-yl (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate収率 39%

実験手順

After 0.26 g of (RS)-3-isopropyl-4-methylidenecyclopent-2-en-1-ol was dissolved in 5 ml of toluene, 0.23 ml of pyridine was added to the toluene solution. Under ice-water cooling, 0.55 g of (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride was added dropwise to the mixed solution, and then stirred at an ambient temperature for six hours. The reaction solution was poured into ice-water and extracted with ethyl acetate. The ethyl acetate layer was washed successively with 5% aqueous hydrochloric acid, water, and a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the obtained oily substance was subjected to silica gel column chromatography to yield 0.25 g of (RS)-3-isopropyl-4-methylidenecyclopenten-2-yl (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate (Compound No.6). Yield 39% nD26 1.4804

後処理

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed successively with 5% aqueous hydrochloric acid, water
  3. dry with materiala saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  4. customAfter removal of the solvent under reduced pressure

出典と根拠

ORDレコード
ord-5aed0796a69c4616a12bf71c82f0ef00
出典データセット
uspto-grants-1997_09
特許番号
US05672779

反応ノート

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