2-(4-Bromo-2,6-dimethylphenyl)-5-[hydroxy(tetrahydropyran-4-yl)methyl]-3-methoxycyclopent-2-enone → 2-(4-Bromo-2,6-dimethylphenyl)-4-[1-(tetrahydropyran-4-yl)-methylidene]-cyclopentane-1,3-dione

HRID 514201Notes

Reaction equation

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

Participants

Conditions

Temperature: 13 °C

Procedure

A solution of 2-(4-bromo-2,6-dimethylphenyl)-5-[hydroxy(tetrahydropyran-4-yl)methyl]-3-methoxycyclopent-2-enone (16.0 g, 39.0 mmol) in a mixture of acetone (320 ml) and 2N hydrochloric acid (160 ml) is heated at 13°C. under microwave irradiation for 40 minutes. Volatile solvents are removed in vacuo, followed by the addition of distilled water (250 ml) and extraction with ethyl acetate (3×150 ml). The combined organic extracts are washed with water, brine, dried over sodium sulphate, then filtered and the filtrate concentrated in vacuo. The residue is finally purified by flash column chromatography to afford 2-(4-bromo-2,6-dimethylphenyl)-4-[1-(tetrahydropyran-4-yl)methylidene]cyclopentane-1,3-dione.

Workup

customVolatile solvents are removed in vacuo
additionfollowed by the addition of distilled water (250 ml) and extraction with ethyl acetate (3×150 ml)
washThe combined organic extracts are washed with water, brine
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationthe filtrate concentrated in vacuo
customThe residue is finally purified by flash column chromatography

Sources & evidence

ORD record: ord-259ff0919b77482493e840570eb12de8
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09107415B2

Reaction notes

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