반응 #155823

반응 방정식

methyl p-hydroxybenzoate

1,5-pentanediol

triphenylphosphine

→

title compound

수율 68.0%

Methyl 4-[(5-hydroxypentyl)oxy]benzoate

수율 68.0%

용매

tetrahydrofuran

diethylazodicarboxylate

반응 조건

후처리

1. 1
   농축The reaction mixture was concentrated
2. 2
   세척the residue was washed with n-hexane-ethyl acetate solution (n-hexane:ethyl acetate=1:1)
3. 3
   농축The reaction mixture was concentrated
4. 4
   기타purified by silica gel chromatography (n-hexane:ethyl acetate=64:36→45:55)

실험 절차

To a solution of methyl p-hydroxybenzoate (3.38 g), 1,5-pentanediol (2.30 g) and triphenylphosphine (5.96 g) in tetrahydrofuran (100 mL), diethylazodicarboxylate (2.2N toluene solution, 10 mL) was slowly added under ice cooling. The reaction mixture was stirred under ice cooling for 16 hours. The reaction mixture was concentrated and the residue was washed with n-hexane-ethyl acetate solution (n-hexane:ethyl acetate=1:1). The reaction mixture was concentrated and then purified by silica gel chromatography (n-hexane:ethyl acetate=64:36→45:55) to obtain the title compound (3.58 g) having the following physical properties.

출처