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

HRID 1193046Notes

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

Participants

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

customThe organic phase is separated
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
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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