1-(3,4,5-Trimethoxyphenyl)-2-propyn-1-ol → 1-(3,4,5-Trimethoxyphenyl)prop-2-yn-1-one

HRID 273344Notes

Reaction equation

HRID 273344 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]([OH:16])[C:14]#[CH:15])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]>CC(C)=O.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:13](=[O:16])[C:14]#[CH:15])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

4

Reactant 1

HCID 161103271-(3,4,5-Trimethoxyphenyl)-2-propyn-1-ol

Product 1

HCID 866061891-(3,4,5-Trimethoxyphenyl)prop-2-yn-1-oneYield 76.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 131709961Jones' reagentSolvent

Procedure

To a stirred solution of 1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ol (100 mg, 0.44 mmol) in acetone (10 mL), aqueous Jones reagent was added dropwise at 0° C. until the red color persisted. The reaction mixture was quenched by 2-propanol, and the precipitate was were removed by filtered through Celite. The filtrate was diluted with EtOAc, washed several times with a saturated aqueous NaHCO3 solution, water and brine, dried over MgSO4, and concentrated to give crude product, which was purified by flash chromatography eluting with EtOAc/n-hexane (1:4) to afford 1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one as a colorless oil (74 mg, 75%).

Workup

  1. customThe reaction mixture was quenched by 2-propanol
  2. customthe precipitate was were removed
  3. filtrationby filtered through Celite
  4. additionThe filtrate was diluted with EtOAc
  5. washwashed several times with a saturated aqueous NaHCO3 solution, water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customto give crude product, which
  9. customwas purified by flash chromatography
  10. washeluting with EtOAc/n-hexane (1:4)

Sources & evidence

ORD record
ord-903bab5e1d8e41eca80090e94c6a643f
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Reaction notes

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