Réaction #5366

Équation de réaction

Cis-nonen-1-ol

sodium bicarbonate

sodium bromide

→

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

Solvants

dichloromethane

NaOCl

water

Conditions de réaction

Traitement

1. 1
   Autredescribed in the preparation of Example 52
2. 2
   workup.ADDITIONTo this mixture is added 1.50 g of Aliquot 336
3. 3
   Autreseparated from the organic phase
4. 4
   Extractionextracted three times with dichloromethane
5. 5
   LavageThe combined organic layers are washed with water
6. 6
   Séchagedried over MgSO4
7. 7
   Concentrationconcentrated in vacuo

Mode opératoire

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.

Source