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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
ノート
印刷プレビュー

反応式

HRID 1919758 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 25953Cesium fluorideHCID 5355539(Z)-Prop-1-en-1-ylboronic acidHCID 59234900HCID 59234900、化合物

生成物 1

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

試薬・触媒・溶媒 2

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

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-777abd5c36164d63940b4d099d1284f3
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08168666B2

反応ノート

読み込み中…

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