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

HRID 1079010노트

반응식

HRID 1079010 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-dimeth ylcyclopropanecarboxylic acid chloride was added drop-wise 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-dimethylcyclopropanecarb oxylate (Compound No.6). Yield 39%

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-89640d4d33164a898b188614c7f285d5
출처 데이터셋
uspto-grants-1996_08
특허 번호
US05550258

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