Reaktion #1119680

Reaktionsgleichung

furfural dimethyl acetal

propargyl aluminum bromide

propargyl bromide

aluminum

→

desired compound

4-(2-Furyl)-4-methoxy-1-butyne

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile maintaining a temperature of
2. 2
   Sonstige25° to 30° C
3. 3
   Sonstigepartitioned with ether and ice-water
4. 4
   SonstigeThe organic layer was separated
5. 5
   Waschenwashed with water
6. 6
   Trocknenaqueous sodium bicarbonate, finally with brine and dried
7. 7
   SonstigeAfter evaporation the residue
8. 8
   workup.DISTILLATIONwas distilled

Vorschrift

To a stirred solution of propargyl aluminum bromide, prepared from 52.9 g of 80% propargyl bromide in toluene, 6.41 g of aluminum splutters activated with 70 mg of mercuric choride and 80 ml of tetrahydrofuran, was added dropwise a solution of 42.2 g of furfural dimethyl acetal [J. Org. Chem., 40, 1478 (1975)] in 30 ml of tetrahydrofuran during a 15 minute period while maintaining a temperature of. 25° to 30° C. The mixture was stirred for 20 minutes at 25° C., then partitioned with ether and ice-water. The organic layer was separated, washed with water, then aqueous sodium bicarbonate, finally with brine and dried. After evaporation the residue was distilled, giving 39.8 g of the desired compound, bp 68°-69° C. (11 mm).

Quelle