반응 #5366

반응 방정식

Cis-nonen-1-ol

sodium bicarbonate

sodium bromide

→

cis-2-(2'-pentylcyclopropyl)acetic acid

용매

dichloromethane

NaOCl

water

반응 조건

후처리

1. 1
   기타described in the preparation of Example 52
2. 2
   workup.ADDITIONTo this mixture is added 1.50 g of Aliquot 336
3. 3
   기타separated from the organic phase
4. 4
   추출extracted three times with dichloromethane
5. 5
   세척The combined organic layers are washed with water
6. 6
   건조dried over MgSO4
7. 7
   농축concentrated in vacuo

실험 절차

Cis-nonen-1-ol (10.0 g) is subjected to the cyclopropanation conditions described in the preparation of Example 52. The resulting residue is taken up in 100 mL of dichloromethane at 0° C., followed by the addition of 800 mg of sodium bromide in 2 mL of water and 150 mg of 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical. To this mixture is added 1.50 g of Aliquot 336 followed by the dropwise addition of 9.2 g of sodium bicarbonate in 230 mL of 5% NaOCl. The aqueous phase is made basic, separated from the organic phase and acidified with concentrated HCl, and then extracted three times with dichloromethane. The combined organic layers are washed with water, dried over MgSO4, and concentrated in vacuo to give cis-2-(2'-pentylcyclopropyl)acetic acid.

출처