Reaktion #522985

Reaktionsgleichung

sodium hydride

sodium hydroxide

2-(formylmethyl)-3-(1-trans-octenyl)-1,1-dioxolano cyclopentane

4-carboxybutyltriphenyl phosphonium bromide

→

2-(6-carboxy-2-cis-hexenyl)-3-(1-trans-octenyl)-1,1-dioxolano cyclopentane

Lösungsmittel

dimethylsulfoxide

dimethylsulfoxide

dimethylsulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA mixture of 0.194 g
2. 2
   TemperaturThe resulting solution is cooled below room temperature
3. 3
   workup.ADDITIONtreated with a solution of 1.400 g
4. 4
   workup.ADDITIONTo the resulting red solution is added 0.738 g
5. 5
   workup.ADDITIONis added to pH 12
6. 6
   Extraktionthe neutral materials are extracted with diethyl ether
7. 7
   Extraktionis extracted with diethyl ether
8. 8
   WaschenThe organic phase is washed with water and saturated brine
9. 9
   Trocknendried (Na2SO4)
10. 10
    Sonstigeevaporated to a semicrystalline mass
11. 11
    SonstigeThe latter is triturated with hot hexane
12. 12
    Filtrationthe solids are filtered off
13. 13
    Sonstigethe filtrate is evaporated
14. 14
    Sonstigeto yield an oil

Vorschrift

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 0.738 g. (0.00263 mole) of 2-(formylmethyl)-3-(1-trans-octenyl)-1,1-dioxolano cyclopentane 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 an oil. IR: 1705, 1040, 970, 722 cm-1.

Quelle