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

HRID 273344

反応式

HRID 273344 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 131709961Jones' reagent溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-903bab5e1d8e41eca80090e94c6a643f
出典データセット
uspto-grants-2008_11
特許番号
US07456289B2

関連ノート

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