Réaction #48666

Équation de réaction

trichloroacetyl chloride

3,3-dimethyl-1-butene

ethylene glycol dimethyl ether

→

desired compound

3-tert-butyl-2,2-dichlorocyclobutanone

Solvants

diethyl ether

diethyl ether

Conditions de réaction

Traitement

1. 1
   TempératureHeat
2. 2
   Températureto reflux for 24 hours
3. 3
   Filtrationfilter off the residual solid materials
4. 4
   ConcentrationConcentrate the filtrate
5. 5
   Autretriturate the residue with hexanes
6. 6
   FiltrationFilter the mixture
7. 7
   Autreto remove solid materials
8. 8
   LavageWash the filtrate solution with saturated aqueous sodium bicarbonate solution (3×), saturated aqueous sodium chloride solution
9. 9
   Séchagedry (magnesium sulfate)
10. 10
    Filtrationfilter
11. 11
    Concentrationconcentrate
12. 12
    Autrepurify
13. 13
    Lavage(silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes)
14. 14
    Autreto give the pure fractions
15. 15
    Concentrationconcentrate

Mode opératoire

Suspend 3,3-dimethyl-1-butene (10 mL, 80.8 mmol), ethylene glycol dimethyl ether (11.5 mL, 106 mmol), and freshly activated zinc (13.8 g, 211 mmol) in dry diethyl ether (100 mL) under a nitrogen atmosphere. Add to this suspension a solution of trichloroacetyl chloride (11.5 mL, 103 mmol) in dry diethyl ether (50 mL) dropwise over 20 minutes. Heat to reflux for 24 hours. Cool to room temperature and filter off the residual solid materials. Concentrate the filtrate and triturate the residue with hexanes. Filter the mixture to remove solid materials. Wash the filtrate solution with saturated aqueous sodium bicarbonate solution (3×), saturated aqueous sodium chloride solution, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes) to give the pure fractions and concentrate. Isolate the desired compound by vacuum distillation to give a clear liquid (7.59 g, 48%).

Source