Reacción #95282

Ecuación de reacción

sodium hydride

4-carboxybutyltriphenyl phosphonium bromide

2-formylmethylcyclopent-2-en-1-one

sodium hydroxide

→

product

2-(6-carboxy-2-cis-hexenyl)-cyclopent-2-en-1-one

Disolventes

dimethylsulfoxide

dimethylsulfoxide

dimethylsulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONA mixture of 0.194 g
2. 2
   TemperaturaThe resulting solution is cooled below room temperature
3. 3
   workup.ADDITIONtreated with a solution of 1.400 g
4. 4
   workup.ADDITIONis added to pH 12
5. 5
   Extracciónthe neutral materials are extracted with diethyl ether
6. 6
   Extracciónis extracted with diethyl ether
7. 7
   LavadoThe organic phase is washed with water and saturated brine
8. 8
   Secadodried (Na2SO4)
9. 9
   Otroevaporated to a semicrystalline mass
10. 10
    OtroThe latter is triturated with hot hexane
11. 11
    Filtraciónthe solids are filtered off
12. 12
    Otrothe filtrate is evaporated

Procedimiento

A mixture of 0.194 g. (0.007952 mole) of sodium hydride (free of mineral oil) and 5.5 ml. of dimethylsulfoxide is heated to 70° C. until gas evolution ceases under a nitrogen atmosphere. The resulting solution is cooled below room temperature and treated with a solution of 1.400 g. (0.00316 mole) of 4-carboxybutyltriphenyl phosphonium bromide [E. J. Corey et al., J. Am. Chem. Soc., 91, 5675 (1969)] in 6 ml. of dimethylsulfoxide. To the resulting red solution is added 0.00263 mole of 2-formylmethylcyclopent-2-en-1-one (Example 898) in 2 ml of dimethylsulfoxide and the mixture is stirred at room temperature for 2.25 hours. The mixture is poured into ice water, sodium hydroxide solution is added to pH 12, and the neutral materials are extracted with diethyl ether. The basic phase is acidified with dilute hydrochloric acid and is extracted with diethyl ether. The organic phase is washed with water and saturated brine, dried (Na2SO4), and evaporated to a semicrystalline mass. The latter is triturated with hot hexane, the solids are filtered off, and the filtrate is evaporated to yield the subject product as an oil.

Fuente