5-Methylfurfural → 1-(5-Methylfuran-2-yl)but-3-yn-1-ol

Temperature

10 °C

In the same flask as in Example 1, there were charged granular magnesium (24.3 g), dry zinc bromide (16.9 g) and dry tetrahydrofuran (110 g). Propargyl chloride (0.55 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 5-methylfurfural (55.06 g), propargyl chloride (47.9 g) and tetrahydrofuran (110 g) was dropwise added to the reaction mixture at 35° C. in 2 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 to give 2-(1-hydroxy-3-butynyl)-5-methylfuran (60.3 g) in a yield of 81% (based on the starting 5-methylfurfural).

1. additionwas dropwise added to the reaction mixture at 35° C. in 2 hours
2. stirringwhile stirring
3. temperatureunder cooling
4. stirringwhile stirring
5. customAfter completion of the reaction
6. additionthe reaction mixture was treated in the same manner as in Example 1

ORD record

ord-54243eb0d5c14992899adfac3af73108

Source dataset

uspto-grants-1990_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04958033