HCID 53714028, compound → Cyclopentaneacetic acid, 3-oxo-2-propyl-, methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH2:9][CH2:8][C:7](=[O:10])[C:6]=1[CH2:11][CH2:12][CH3:13].[H][H]>>[CH2:11]([CH:6]1[C:7](=[O:10])[CH2:8][CH2:9][CH:5]1[CH2:4][C:3]([O:2][CH3:1])=[O:14])[CH2:12][CH3:13]Participants
3
Conditions
- Temperature
- 40 °C
Procedure
Into a 1 liter flask purged with dry nitrogen, there is introduced 210 ml of anhydrous methanol followed by 63.2 g of aluminium triisobutyl over thirty minutes. The resulting solution is refluxed for one hour. After cooling, the solution is introduced into an autoclave with 6.5 g of 5.3% palladium on carbon. 58.8 g (0.30 mole) of methyl[2-n-propyl-3-keto-cyclopent-1-en-1-yl]-acetate is added. The autoclave is closed, shaken to homogenise the mass and heated to 40°C. Hydrogen is then introduced under a pressure of 10 kg/cm2 until no further hydrogen absorption occurs. After cooling, the mass is filtered to separate the catalyst, poured into water and extracted with petroleum ether (3 × 100 ml). The petroleum ether solution is washed to neutrality and distilled. 53 g of crude product are thus obtained which are rectified under reduced pressure. 43.8 g of methyl [2-n-propyl-3-keto-cyclopent-1-yl]-acetate is thus obtained, presenting the following characteristics: