Rac-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone → HCID 89600897, compound

HRID 514197Notes

Reaction equation

HRID 514197 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][CH3:10])[CH:5]=[C:4]([CH3:11])[C:3]=1[C:12]1[C:13](=[O:26])[CH:14]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:15][C:16]=1[O:17]C>CC(C)=O.Cl>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][CH3:10])[CH:5]=[C:4]([CH3:11])[C:3]=1[CH:12]1[C:13](=[O:26])[CH:14]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:15][C:16]1=[O:17]

Participants

4

Reactant 1

HCID 89600971Rac-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone

Product 1

HCID 89600897HCID 89600897, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of rac-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone (0.5 g, 1.45 mmol) in acetone (10 ml) and 2N hydrochloric acid (5 ml) is heated at 80°C. under microwave irradiation for 40 minutes. Volatile solvents are removed in vacuo and residue is diluted with distilled water (50 ml) and extracted with ethyl acetate (3×50 ml). The combined organic fractions are washed again with distilled water, brine, dried over sodium sulfate, filtered and the filtrate concentrated in vacuo. The crude product is purified by flash column chromatography to afford rac-2-(2,6-Dimethyl-4-prop-1-ynylphenyl)-4-pyridin-2-ylmethylcyclopentane-1,3-dione.

Workup

  1. customVolatile solvents are removed in vacuo and residue
  2. additionis diluted with distilled water (50 ml)
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. washThe combined organic fractions are washed again with distilled water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customThe crude product is purified by flash column chromatography

Sources & evidence

ORD record
ord-ac0e587f98fc4228b286f8fcc785b8aa
Source dataset
uspto-grants-2015_08
Patent number
US09107415B2

Reaction notes

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