Reaction #487518

Reaction equation

7-hydroxycoumarin

NaH

4-bromo-1-butene

→

4-(7-coumarinyloxy)-1-butene

Yield 67.0%

Solvents

DMF

ethyl acetate

Conditions

Workup

1. 1
   Washis washed with water (3×300 mL)
2. 2
   OtherThe residue is chromatographed with the mixture (ethyl acetate-hexane)

Procedure

A suspension of 7-hydroxycoumarin (3 g, 19.6 mmol) in DMF (20 ml) is treated with NaH (60% suspension in oil, 1.03 g, 25.9 mmol), then with 4-bromo-1-butene (2.65 g, 19.6 mmol). It is heated to 60° C. for 24 hours, then it is diluted with ethyl acetate (400 ml), and it is washed with water (3×300 mL) then with 1 M NaOH (3×200 ml). The residue is chromatographed with the mixture (ethyl acetate-hexane) to obtain 4-(7-coumarinyloxy)-1-butene (2.7 g, 67%).

Source