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

HRID 2291903노트

반응식

HRID 2291903 반응식
[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]

참가 물질

5

반응물 3

HCID 962Water2회HCID 7918Acetic AnhydrideHCID 143028923-Acetyl-3a,7a-dihydro-7a-(phenylethynyl)benzofuran-2,5(3H,4H)-dione

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4a7df22fec6148c5b2d23c7b9e8fab43
출처 데이터셋
uspto-grants-1989_01
특허 번호
US04798893

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