Furfural → 1-(2-Furyl)but-3-yn-1-ol

Participants

Reaction Conditions

Reaction Steps

In the same flask as in Example 1, there were charged granular magnesium (18.2 g), dry zinc chloride (10.2 g) and dry tetrahydrofuran (110 g). Propargyl bromide (0.88 g) was added thereto at 10° C while stirring. The resultant mixture was kept in an adiabatic condition, whereupon the reaction proceeded. When the heat generation stopped, a mixture of furfural (48.0 g), propargyl bromide (73.5 g) and toluene (110 g) was dropwise added to the reaction mixture at 30° C in 3 hours while stirring under cooling. The resultant mixture was kept at room temperature for 30 minutes while stirring. After completion of the reaction, the reaction mixture was treated in the same manner as in Example 1 and distilled under reduced pressure (65°-66° C./ 0.45 mmHg) to give 2-(1-hydroxy-3-butynyl)-furan (61.3 g) in a yield of 90% (based on the starting furfural).

Provenance & Evidence