Réaction #6593

Équation de réaction

4-(dimethylamino)benzyl alcohol

3-hydroxybenzaldehyde

triphenylphosphine

→

3-(4-(dimethylamino)-benzyloxy) benzaldehyde

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   ConcentrationConcentrate the solution in vacuo
2. 2
   workup.ADDITIONdilute with a small quantity of ethyl ether
3. 3
   FiltrationFilter any precipitate
4. 4
   Concentrationconcentrate the filtrat in vacuo
5. 5
   AutrePurify by silica gel chromatography

Mode opératoire

Mix 4-(dimethylamino)benzyl alcohol (3.35 g. 22 mmol), 3-hydroxybenzaldehyde (2.69 g, 22 mmol), triphenylphosphine (5.8 g, 22 mmol) and diethylazadicarboxylate (3.83 g, 22 mmol) in tetrahydrofuran (25 mL). Stir at room temperature under anhydrous atmosphere until the reaction is done. Concentrate the solution in vacuo and dilute with a small quantity of ethyl ether. Filter any precipitate and concentrate the filtrat in vacuo. Purify by silica gel chromatography to give 3-(4-(dimethylamino)-benzyloxy) benzaldehyde.

Source