Propargyl bromide → 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 (14.6 g), dry zinc chloride (6.8 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 5-methylfurfural (55.06 g), propargyl bromide (64.5 g), tetrahydrofuran (55 g) and isopropyl ether (55 g) was dropwise added to the reaction mixture at 50° C. in 1.5 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 (60.5 g) in a yield of 81% (based on the starting 5-methylfurfural).

1. additionwas dropwise added to the reaction mixture at 50° C. in 1.5 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-15edd6bc59dc4428bbb802a9b314251a

Source dataset

uspto-grants-1990_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04958033