Reacción #938517

Ecuación de reacción

Methyllithium

6,6-ethylenedioxy-2-methyl-2-(4'-oxobutyl)-oxepane

→

6,6-ethylenedioxy-2-(4'-hydroxypentyl)-2-methyloxepane

Rendimiento 94.0%

6,6-Ethylenedioxy- 2-(4'-hydroxypentyl)-2-methyloxepane

Rendimiento 94.0%

Disolventes

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe cooling bath is removed
2. 2
   workup.ADDITIONThe mixture is poured into cold satd
3. 3
   OtroThe ether layer is separated
4. 4
   Extracciónthe aqueous layer extracted with ether (3×50 ml)
5. 5
   Secadodried (MgSO4)
6. 6
   Otrothe solvent is removed at reduced pressure
7. 7
   OtroThe crude product (3.6 g) is chromatographed on SilicAR CC-7 (70 g) in hexane
8. 8
   LavadoElution with 15% ethyl acetate/hexane

Procedimiento

Methyllithium (10 ml, 0.0184 mol, 1.84 M in hexane) is added dropwise to a solution of 6,6-ethylenedioxy-2-methyl-2-(4'-oxobutyl)-oxepane (3.3 g) in ether (150 ml) at 0° C. in a nitrogen atmosphere. The cooling bath is removed and the mixture is stirred for 0.5 hour at ambient temperature. The mixture is poured into cold satd. NaCl (300 ml). The ether layer is separated and the aqueous layer extracted with ether (3×50 ml). The ether phases are combined, dried (MgSO4) and the solvent is removed at reduced pressure. The crude product (3.6 g) is chromatographed on SilicAR CC-7 (70 g) in hexane. Elution with 15% ethyl acetate/hexane gives 6,6-ethylenedioxy-2-(4'-hydroxypentyl)-2-methyloxepane (15) as a clear colorless oil (3.3 g, 94%).

Fuente