5-(4-Fluoro-benzyl)-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone → 4-(4-Fluoro-benzyl)-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione

HRID 1631885Notes

Reaction equation

[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][CH:7]2[C:11](=[O:12])[C:10]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])=[C:9]([O:22]C)[CH2:8]2)=[CH:4][CH:3]=1>CC(C)=O.Cl>[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][CH:7]2[CH2:8][C:9](=[O:22])[CH:10]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:11]2=[O:12])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 5-(4-fluoro-benzyl)-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (136 mg, 0.40 mmol) in acetone (2 ml) is added a 2N solution of hydrochloric acid (2 ml) and the resulting solution is heated to 40° C. by microwave irradiation for 30 minutes. The reaction mixture is diluted with 2N hydrochloric acid (25 ml), and extracted with ethyl acetate (2×25 ml). The combined organics are washed with brine (25 ml), dried over magnesium sulphate, filtered and concentrated in vacuo to give 4-(4-fluoro-benzyl)-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione (124 mg).

Workup

extractionextracted with ethyl acetate (2×25 ml)
washThe combined organics are washed with brine (25 ml)
dry with materialdried over magnesium sulphate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1529d5ab2a904ecf94937effc348343b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791303B2

Reaction notes

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