2-(4-Bromo-2,6-dimethylphenyl)-3-methoxy-5-[1-pyridin-2-ylmethylidene]cyclopent-2-enone → Rac-2-(4-bromo-2,6-dimethylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone

HRID 514195Notes

Reaction equation

HRID 514195 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:10](=[O:23])[C:11](=[CH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:12][C:13]=2[O:14][CH3:15])=[C:4]([CH3:24])[CH:3]=1>C(O)(=O)C.[Zn]>[Br:1][C:2]1[CH:3]=[C:4]([CH3:24])[C:5]([C:9]2[C:10](=[O:23])[CH:11]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:12][C:13]=2[O:14][CH3:15])=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 1

HCID 896012732-(4-Bromo-2,6-dimethylphenyl)-3-methoxy-5-[1-pyridin-2-ylmethylidene]cyclopent-2-enone

Product 1

HCID 89600800Rac-2-(4-bromo-2,6-dimethylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
27.5 °C

Procedure

To a solution of 2-(4-bromo-2,6-dimethylphenyl)-3-methoxy-5-[1-pyridin-2-ylmethylidene]cyclopent-2-enone (2.8 g, 7.3 mmol) in acetic acid (30 ml) is added zinc powder (2.3 g, 36.5 mmol) at 25-30°C. The resulting suspension is stirred at 25-30°C. for 6-7 hours, then filtered through a bed of diatomaceous earth and washed with methanol (20 ml×2). The filtrate is concentrated under vacuum, water is added and the crude product is extracted with ethyl acetate (50 ml×3). The combined organic fractions are washed with distilled water, brine, dried over sodium sulfate, filtered and the filtrate concentrated in vacuo. The crude is purified by flash column chromatography to afford rac-2-(4-bromo-2,6-dimethylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone.

Workup

  1. filtrationfiltered through a bed of diatomaceous earth
  2. washwashed with methanol (20 ml×2)
  3. concentrationThe filtrate is concentrated under vacuum, water
  4. additionis added
  5. extractionthe crude product is extracted with ethyl acetate (50 ml×3)
  6. washThe combined organic fractions are washed with distilled water, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated in vacuo
  10. customThe crude is purified by flash column chromatography

Sources & evidence

ORD record
ord-87e37a4ea38449e5bfaf055355f0f61e
Source dataset
uspto-grants-2015_08
Patent number
US09107415B2

Reaction notes

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