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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 514201
Notes
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Reaction equation

HRID 514201 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 896013392-(4-Bromo-2,6-dimethylphenyl)-5-[hydroxy(tetrahydropyran-4-yl)methyl]-3-methoxycyclopent-2-enone

Product 1

HCID 671097292-(4-Bromo-2,6-dimethylphenyl)-4-[1-(tetrahydropyran-4-yl)-methylidene]-cyclopentane-1,3-dione

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

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

  1. customVolatile solvents are removed in vacuo
  2. additionfollowed by the addition of distilled water (250 ml) and extraction with ethyl acetate (3×150 ml)
  3. washThe combined organic extracts are washed with water, brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes