반응 #2473

반응 방정식

ether

(CH3)2SO4

(±)cis-3-oxo-2-pentyl-1-cyclopentaneacetic acid

→

methyl (±)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate

수율 89.8%

용매

water

(CH3)2CO

반응 조건

후처리

1. 1
   기타The ether phase was separated
2. 2
   추출the aqueous phase once more extracted with ether
3. 3
   세척The combined organic phases were washed with water
4. 4
   건조dried over MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   workup.DISTILLATIONThe residue was distilled in a bulb-to-bulb apparatus (oven t.: 180°/7 Pa)

실험 절차

To 104 mg (0.49 mmole) of (±)cis-3-oxo-2-pentyl-1-cyclopentaneacetic acid (93:7 cis/trans ratio) in 1 ml of (CH3)2CO there were added, first 56 μl of (CH3)2SO4 (74 ml, 0.59 mmole, 1.2 eq.) and then 81 mg (0.59 mmole, 1.2 eq.) of anhydrous solid K2 CO3. The resulting suspension was heated at r.t. during 4 h and taken in water and with ether. The ether phase was separated and the aqueous phase once more extracted with ether. The combined organic phases were washed with water, dried over MgSO4, filtered and concentrated. The residue was distilled in a bulb-to-bulb apparatus (oven t.: 180°/7 Pa) to provide 93 mg (0.44 mmole, yield 84%) of methyl (±)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate (92/8 cis/trans ratio).

출처