Sulfuric Acid → 9-Cycloheptadecen-1-one
Reaction equation
COC([CH:5]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH:15]=[CH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:22])=O.S(=O)(=O)(O)O>[OH-].[Na+].C(O)C.C1COCC1>[C:6]1(=[O:22])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:5]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
2-Methoxycarbonyl-9-cycloheptadecenone (92 mg, 0.30 mmol) was dissolved in a mixed solvent of 5% aqueous NaOH/ethanol/THF (2.5:5.0:2.5, vol./vol./vol.) and the solution was refluxed at 80° C. for 5 hours. After cooling to 0° C., the reaction solution was rendered slightly acidic using 10% sulfuric acid aqueous solution and the whole was further refluxed for 10 minutes. After the evaporation of the solvent under reduced pressure, the residue was extracted with ether. The organic layer was washed with saturated sodium hydrogen carbonate aqueous solution, water, and saturated brine, and then dried over anhydrous sodium sulfate. After the evaporation of the solvent under reduced pressure, the crude product was purified by silica gel chromatography (hexane/ethyl acetate=40/1) to obtain the aimed product (71 mg, 95%)
Workup
- temperatureAfter cooling to 0° C.
- temperaturethe whole was further refluxed for 10 minutes
- customAfter the evaporation of the solvent under reduced pressure
- extractionthe residue was extracted with ether
- washThe organic layer was washed with saturated sodium hydrogen carbonate aqueous solution, water, and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customAfter the evaporation of the solvent under reduced pressure
- customthe crude product was purified by silica gel chromatography (hexane/ethyl acetate=40/1)
Sources & evidence
- ORD record
- ord-2c83173de6b44c89aab0963c9e14ac18
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06861551B2
Reaction notes
Loading…