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Hydrochloric Acid → 2-[4-(4-Chlorophenoxy)-2-ethylphenyl]-3-hydroxycyclopent-2-enone

HRID 1193046
ノート
印刷プレビュー

反応式

HRID 1193046 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12](=[O:13])[CH2:11][CH2:10][C:9]2=[O:14])=[C:4]([CH2:15][CH3:16])[CH:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>[O-]S(C(F)(F)F)(=O)=O.[Cu+2].[O-]S(C(F)(F)F)(=O)=O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[C:12](=[O:13])[CH2:11][CH2:10][C:9]=3[OH:14])=[C:4]([CH2:15][CH3:16])[CH:3]=2)=[CH:20][CH:19]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 46844-ChlorophenolHCID 10796Cesium carbonateHCID 667097952-(4-Bromo-2-ethylphenyl)cyclopentane-1,3-dione

生成物 1

HCID 580708502-[4-(4-Chlorophenoxy)-2-ethylphenyl]-3-hydroxycyclopent-2-enone

試薬・触媒・溶媒 3

HCID 2734996
copper(II) trifluoromethanesulfonate
触媒
HCID 1140Toluene溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
16 °C

実験手順

To a mixture of 2-(4-bromo-2-ethylphenyl)cyclopentane-1,3-dione (0.20 g, 0.0007 mol), 4-chlorophenol (0.180 g, 0.0014 mol), cesium carbonate (0.460 g, 0.0014 mol), copper triflate (10 mg, 0.00003 mol) and activated 4 Å molecular sieves (0.30 g) is added anhydrous toluene (7 ml). The mixture is then heated at 16° C. for 1 hour under microwave irradiation, followed by dilution with ethyl acetate (50 ml) and 2M hydrochloric acid (50 ml). The organic phase is separated, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product is purified by preparative reverse phase HPLC to afford 2-[4-(4-chlorophenoxy)-2-ethylphenyl]-3-hydroxycyclopent-2-enone as a cream solid.

後処理

  1. customThe organic phase is separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product is purified by preparative reverse phase HPLC

出典と根拠

ORDレコード
ord-f207e34d08a441acb6b233047b457034
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08680339B2

反応ノート

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