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

HRID 1193046
Notes
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Reaction equation

HRID 1193046 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 2734996
copper(II) trifluoromethanesulfonate
Catalyst
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
16 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f207e34d08a441acb6b233047b457034
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08680339B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes