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Triphenylphosphine → (2,3,5,6-tetrafluorophenyl)methyl (1R)-trans-2,2-dimethyl-3-((Z)-1-propenyl)cyclopropanecarboxylate

HRID 1976310
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HRID 1976310 반응식
[CH3:1][C:2]1([CH3:11])[C@H:4](/[CH:5]=[CH:6]\[CH3:7])[C@H:3]1[C:8]([OH:10])=[O:9].[F:12][C:13]1[C:18]([F:19])=[CH:17][C:16]([F:20])=[C:15]([F:21])[C:14]=1[CH2:22]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1.O1CCCC1>[CH3:11][C:2]1([CH3:1])[C@H:4](/[CH:5]=[CH:6]\[CH3:7])[C@H:3]1[C:8]([O:10][CH2:22][C:14]1[C:15]([F:21])=[C:16]([F:20])[CH:17]=[C:18]([F:19])[C:13]=1[F:12])=[O:9]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 27340292,3,5,6-Tetrafluorobenzyl alcoholHCID 45084794(1R)-trans-2,2-dimethyl-3-((Z)-1-propenyl)cyclopropanecarboxylic acid

생성물 1

HCID 23730913(2,3,5,6-tetrafluorophenyl)methyl (1R)-trans-2,2-dimethyl-3-((Z)-1-propenyl)cyclopropanecarboxylate수율 93%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture solution of 0.42 g of (1R)-trans-2,2-dimethyl-3-((Z)-1-propenyl)cyclopropanecarboxylic acid, 0.49 g of (2,3,5,6-tetrafluorophenyl)methanol, 0.93 g of triphenylphosphine and 20 ml of tetrahydrofuran, 2.0 ml of 40% toluene solution containing diisopropyl azodicarboxylate was added. After one day, the reaction solution was concentrated under reduced pressure and the residue was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=20/1) to give 0.80 g of (2,3,5,6-tetrafluorophenyl)methyl (1R)-trans-2,2-dimethyl-3-((Z)-1-propenyl)cyclopropanecarboxylate

후처리

  1. additionwas added
  2. concentrationthe reaction solution was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-7810489b3e7044ab84a101a158b2368a
출처 데이터셋
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06225495B1

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