(2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R)-trans-3-formyl-2,2-dimethylcyclopropanecarboxylate → Fairytale

HRID 1976309노트

반응식

HRID 1976309 반응식
[CH3:1][C:2](C)([O-])C.[K+].[CH:7]([C@@H:9]1[C@@H:11]([C:12]([O:14][CH2:15][C:16]2[C:21]([F:22])=[C:20]([F:23])[C:19]([CH3:24])=[C:18]([F:25])[C:17]=2[F:26])=[O:13])[C:10]1([CH3:28])[CH3:27])=O>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.O1CCCC1>[CH3:27][C:10]1([CH3:28])[C@H:9](/[CH:7]=[CH:1]\[CH3:2])[C@H:11]1[C:12]([O:14][CH2:15][C:16]1[C:21]([F:22])=[C:20]([F:23])[C:19]([CH3:24])=[C:18]([F:25])[C:17]=1[F:26])=[O:13]

참가 물질

5

반응물 2

HCID 15451879(2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R)-trans-3-formyl-2,2-dimethylcyclopropanecarboxylateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 23731026Fairytale수율 67%

시약·촉매·용매 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

A mixture of 1.1 g of ethyltriphenylphosphonium bromide and 30 ml of terahydrofuran was cooled by ice and 0.23 g of potassium tert-butoxide was added to the mixture under stirring. After 15 minutes, a tetrahydrofuran (5 ml) solution containing 0.32 g of (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R)-trans-3-formyl-2,2-dimethylcyclopropanecarboxylate was added to the mixture. After 30 minutes, the reaction mixture was filtered with celite and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=20/1) to give 0.22 g of (2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1R)-trans-2,2-dimethyl-3-((Z)-1-propenyl)cyclopropanecarboxylate

후처리

  1. additionwas added to the mixture
  2. additionwas added to the mixture
  3. waitAfter 30 minutes
  4. filtrationthe reaction mixture was filtered with celite
  5. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-404ab1dd152a4a6fb640c8da731a71dc
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06225495B1

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