Hydrochloric Acid → 4-[1-Furan-3-yl-meth-(e)-ylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione

HRID 336086Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][C:3]([CH:6](O)[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:2]1.Cl>CC(C)=O>[O:1]1[CH:5]=[CH:4][C:3](/[CH:6]=[C:7]2/[C:11](=[O:12])[CH: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])[CH2:8]/2)=[CH:2]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 5-(furan-3-yl-hydroxy-methyl)-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (770 mg) in acetone (2 ml) is added 2N hydrochloric acid (2 ml) and the resulting suspension heated to 120° C. for 30 minutes. The crude reaction mixture is concentrated in vacuuo and purified by flash chromatography to give 4-[1-furan-3-yl-meth-(E)-ylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione.

Workup

customThe crude reaction mixture
concentrationis concentrated in vacuuo
custompurified by flash chromatography

Sources & evidence

ORD record: ord-9d20b3f221bf4044bb2301bea69520e5
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889595B2

Reaction notes

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