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

HRID 1379936노트

반응식

HRID 1379936 반응식
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]

참가 물질

5

반응물 4

HCID 1049PyridineHCID 1140Toluene2회HCID 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

생성물 1

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

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-5aed0796a69c4616a12bf71c82f0ef00
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05672779

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