Reacción #455994

Ecuación de reacción

methanesulfonic acid

phenethyl alcohol

3-Chloropropionaldehyde diethyl acetal

→

title compound

[(3-Chloro-1-ethoxypropoxy)ethyl]benzene

Disolventes

nitromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONis added
2. 2
   OtroAfter 30 min the ice bath is removed
3. 3
   TemperaturaThe mixture is then warmed in a water bath at approximately 40-50° under reduced pressure for 10-20 min (
4. 4
   Otrono appreciable removal of nitromethane
5. 5
   OtroThe mixture is partitioned between ethyl ether and saline
6. 6
   Otrothe layers are separated
7. 7
   Secadothe organic phase is dried over megnesium sulfate
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   workup.WAITThe curde material is stored overnight in the refreigerator
10. 10
    Otrochromatographed on silica gel eluting with hexane
11. 11
    Concentraciónconcentrated

Procedimiento

3-Chloropropionaldehyde diethyl acetal (LXII, 30.66 g, 0.184 mol) is added to an ice-cooled solution of phenethyl alcohol (XLV, 20.44 g, 0.167 mol) in nitromethane (50 ml) is added and methanesulfonic acid (1.61 g, 0.0167 mol). After 30 min the ice bath is removed and the mixture is allowed to stir overnight. The mixture is then warmed in a water bath at approximately 40-50° under reduced pressure for 10-20 min (no appreciable removal of nitromethane occurs but there is some further reaction observed). The mixture is partitioned between ethyl ether and saline, the layers are separated and the organic phase is dried over megnesium sulfate and concentrated under reduced pressure. The curde material is stored overnight in the refreigerator and then chromatographed on silica gel eluting with hexane and then ethyl acetate/hexane (2/98). The appropriate fractions are pooled and concentrated to give the title compound, NMR (CDCl3) 1.20, 2.05, 2.87, 3.43-3.86, 4.69 and 7.24 δ.

Fuente