تفاعل #2473

معادلة التفاعل

ether

(CH3)2SO4

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

→

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

المردود 89.8%

المذيبات

water

(CH3)2CO

ظروف التفاعل

المعالجة

1. 1
   أخرىThe ether phase was separated
2. 2
   استخلاصthe aqueous phase once more extracted with ether
3. 3
   غسيلThe combined organic phases were washed with water
4. 4
   تجفيفdried over MgSO4
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated
7. 7
   workup.DISTILLATIONThe residue was distilled in a bulb-to-bulb apparatus (oven t.: 180°/7 Pa)

الإجراء التجريبي

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).

المصدر