Water → 1-[5-Acetoxy-2-(phenylethynyl)phenyl]-2-propanone

HRID 2291903ノート

反応式

HRID 2291903 の反応式
[C:1]([CH:4]1[CH:8]2[CH2:9][C:10](=[O:13])[CH:11]=[CH:12][C:7]2([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)OC1=O)(=[O:3])[CH3:2].[C:23](OC(=O)C)(=[O:25])[CH3:24].O>C(Cl)Cl>[C:23]([O:13][C:10]1[CH:11]=[CH:12][C:7]([C:14]#[C:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:8]([CH2:4][C:1](=[O:3])[CH3:2])[CH:9]=1)(=[O:25])[CH3:24]

参加物

5

反応物 3

HCID 962Water2 回HCID 7918Acetic AnhydrideHCID 143028923-Acetyl-3a,7a-dihydro-7a-(phenylethynyl)benzofuran-2,5(3H,4H)-dione

生成物 1

HCID 212782901-[5-Acetoxy-2-(phenylethynyl)phenyl]-2-propanone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3-Acetyl-3a,7a-dihydro-7a-(phenylethynyl)benzofuran-2,5(3H,4H)dione, the product of Example 1A, (10.0 g, 34 mmole) and acetic anhydride (25 mL) were placed in a 100 mL flask and heated at reflux overnight under argon. Heating was stopped and the reaction was treated with water (25 mL) and stirred for 1 hr. The reaction was poured into water and extracted with Et2O. The combined ether extracts were washed with water and saturated sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and concentrated to yield 9.4 g of crude product. Chromatography of the crude product over silica gel, using methylene chloride as eluent, gave 4.2 g of pure 1-[5-Acetoxy-2-(phenylethynyl)phenyl]-2-propanone product as a viscous oil.

後処理

  1. temperatureheated
  2. temperatureat reflux overnight under argon
  3. temperatureHeating
  4. extractionextracted with Et2O
  5. washThe combined ether extracts were washed with water and saturated sodium bicarbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield 9.4 g of crude product

出典と根拠

ORDレコード
ord-4a7df22fec6148c5b2d23c7b9e8fab43
出典データセット
uspto-grants-1989_01
特許番号
US04798893

反応ノート

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