2,3,4,5,6-Pentafluorobenzyl Alcohol → pentafluorobenzyl (1R,trans) 2,2-dimethyl-3-(1,2-propadienyl)-cyclopropane-carboxylate

HRID 485716

반응식

HRID 485716 반응식
C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][C:17]1([CH3:26])[C@H:19]([CH:20]=[C:21]=[CH2:22])[C@H:18]1[C:23]([OH:25])=[O:24].[F:27][C:28]1[C:33]([CH2:34]O)=[C:32]([F:36])[C:31]([F:37])=[C:30]([F:38])[C:29]=1[F:39]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:16][C:17]1([CH3:26])[C@H:19]([CH:20]=[C:21]=[CH2:22])[C@H:18]1[C:23]([O:25][CH2:34][C:33]1[C:32]([F:36])=[C:31]([F:37])[C:30]([F:38])=[C:29]([F:39])[C:28]=1[F:27])=[O:24]

참가 물질

6

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온도
20 °C

실험 절차

A solution of 4.12 g of dicyclohexylcarbodiimide in 40 ml of methylene chloride was added at 0° C. to a mixture of 3 g of (1R,trans) 2,2-dimethyl-3-(1,2-propadienyl)-cyclopropane-carboxylic acid, 30 ml of methylene chloride, 3.96 g of pentafluorobenzyl alcohol and 100 mg of 4-dimethylaminopyridine and the mixture was stirred at 20° C. for 16 hours and was filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 9-1 hexane-ethyl acetate mixture yielded 4.78 g of pentafluorobenzyl (1R,trans) 2,2-dimethyl-3-(1,2-propadienyl)-cyclopropane-carboxylate with a specific rotation of [α]D20 =-23° (c=0.5% in chloroform).

후처리

  1. filtrationwas filtered
  2. customThe filtrate was evaporated to dryness under reduced pressure
  3. customthe residue was chromatographed over silica gel
  4. washElution with a 9-1 hexane-ethyl acetate mixture

출처 및 근거

ORD 기록
ord-45c6e0aa1d6c4d56b6c6cbcaf5f003a5
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04537897

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