Water → 3-Methyl-2-[6-(m-methoxyphenyl)-2-hydroxy-3-hexynyl]-2-cyclopentenone

HRID 27657노트

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HRID 27657 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]#[C:12][CH:13]([OH:22])[CH2:14][CH2:15][C:16]2[O:17][C:18]([CH3:21])=[CH:19][CH:20]=2)[CH:6]=[CH:7][CH:8]=1.O.S(=O)(=O)(O)O>C(O)(=O)C>[CH3:21][C:18]1[CH2:19][CH2:20][C:16](=[O:17])[C:15]=1[CH2:14][CH:13]([OH:22])[C:12]#[C:11][CH2:10][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1

참가 물질

5

반응물 3

HCID 962Water2회HCID 1118Sulfuric AcidHCID 233414791-(m-Methoxyphenyl)-7-(5-methyl-2-furyl)-3-heptyn-5-ol

생성물 1

HCID 233414893-Methyl-2-[6-(m-methoxyphenyl)-2-hydroxy-3-hexynyl]-2-cyclopentenone

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
80 °C

실험 절차

A solution of 10.00 g (33.6 mmol) dl-1-(m-methoxyphenyl)-7-(5-methyl-2-furyl)-3-heptyn-5-ol in 20 ml acetic acid, about 10 ml water and 0.40 ml about 20% sulphuric acid was stirred under nitrogen in an oil-bath at 90° C. for about 24 hours. After cooling, the mixture was poured into 200 ml water and extracted with methylene chloride. The methylene chloride layer was washed with water and evaporated to dryness under reduced pressure. The residue (10.60 g) was dissolved in 500 ml of about 0.1 N ethanolic potassium hydroxide solution and stirred under nitrogen in an oil-bath at about 80° C. for about 1 hour. After cooling, the mixture was poured into 1000 ml water and extracted with methylene chloride. The methylene chloride layer was washed with water and evaporated to dryness under reduced pressure. Yield: 9.85 g.

후처리

  1. temperatureAfter cooling
  2. extractionextracted with methylene chloride
  3. washThe methylene chloride layer was washed with water
  4. customevaporated to dryness under reduced pressure
  5. dissolutionThe residue (10.60 g) was dissolved in 500 ml of about 0.1 N ethanolic potassium hydroxide solution
  6. temperatureAfter cooling
  7. additionthe mixture was poured into 1000 ml water
  8. extractionextracted with methylene chloride
  9. washThe methylene chloride layer was washed with water
  10. customevaporated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-5fb30ba6d39d469087fc92de1cef87a2
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04222940

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