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Cesium fluoride → 4-[1,1,1,3,3,3-hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-[(1Z)-1-propenyl]-6-propylphenol

HRID 1919758
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HRID 1919758 반응식
[F-].[Cs+].[CH:3](/B(O)O)=[CH:4]/[CH3:5].[F:9][C:10]([F:32])([F:31])[C:11]([C:20]1[CH:25]=[C:24]([CH2:26][CH2:27][CH3:28])[C:23]([OH:29])=[C:22](I)[CH:21]=1)([O:16][CH2:17][O:18][CH3:19])[C:12]([F:15])([F:14])[F:13]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:9][C:10]([F:32])([F:31])[C:11]([C:20]1[CH:25]=[C:24]([CH2:26][CH2:27][CH3:28])[C:23]([OH:29])=[C:22](/[CH:3]=[CH:4]\[CH3:5])[CH:21]=1)([O:16][CH2:17][O:18][CH3:19])[C:12]([F:15])([F:14])[F:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 25953Cesium fluorideHCID 5355539(Z)-Prop-1-en-1-ylboronic acidHCID 59234900HCID 59234900, 화합물

생성물 1

HCID 592350754-[1,1,1,3,3,3-hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-[(1Z)-1-propenyl]-6-propylphenol수율 181.5%

시약·촉매·용매 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 1140Toluene용매

실험 절차

Cesium fluoride (1.24 g), cis-propenylboronic acid (1.54 g) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.49 g) were added to a mixed solution of 4-[1,1,1,3,3,3-hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-iodo-6-propylphenol (2.83 g, 5.99 mmol) in toluene (60 mL) in an argon atmosphere at room temperature, followed by stirring overnight. After completion of the reaction, the reaction solution was extracted with ethyl acetate-water, and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 4.20 g of the title compound (yield: 85%) as a brown solid.

후처리

  1. customAfter completion of the reaction
  2. extractionthe reaction solution was extracted with ethyl acetate-water
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

출처 및 근거

ORD 기록
ord-777abd5c36164d63940b4d099d1284f3
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08168666B2

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