Water → 3-Methyl-2-[6-(m-methoxyphenyl)-2-hydroxy-3-hexynyl]-2-cyclopentenone
Reaction equation
[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]=1Participants
Conditions
- Temperature
- 80 °C
Procedure
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.
Workup
- temperatureAfter cooling
- extractionextracted with methylene chloride
- washThe methylene chloride layer was washed with water
- customevaporated to dryness under reduced pressure
- dissolutionThe residue (10.60 g) was dissolved in 500 ml of about 0.1 N ethanolic potassium hydroxide solution
- temperatureAfter cooling
- additionthe mixture was poured into 1000 ml water
- extractionextracted with methylene chloride
- washThe methylene chloride layer was washed with water
- customevaporated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-5fb30ba6d39d469087fc92de1cef87a2
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04222940
Reaction notes
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