Réaction #46720

Équation de réaction

2-Hydroxy-4-[4-(3-hydroxy-prop-1-ynyl)-benzylamino]-benzoic acid methyl ester

LiOH

→

pure product

Rendement 17.3%

2-Hydroxy-4-[4-(3-hydroxy-prop-1-ynyl)-benzylamino]-benzoic acid

Rendement 17.3%

Solvants

THF H2O

Conditions de réaction

Traitement

1. 1
   AutreTHF was removed by evaporation and EtOAc (3 mL) and H2O (0.5 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   AutreThe organic phase was isolated
4. 4
   Séchagedried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Autreevaporated to dryness
7. 7
   Autrepurified by flash column chromatography (SiO2-PE80-100° C./EtOAc/CH3COOH=1:1:1%)

Mode opératoire

2-Hydroxy-4-[4-(3-hydroxy-prop-1-ynyl)-benzylamino]-benzoic acid methyl ester (22 mg; 0.07 mmol) was dissolved in THF/H2O (1 mL/0.25 mL) and LiOH was added (17 mg; 0.7 mmol). The reaction mixture was heated to 90° C. for 1 hour. THF was removed by evaporation and EtOAc (3 mL) and H2O (0.5 mL) was added. The organic phase was isolated, dried (Na2SO4), filtered, evaporated to dryness and purified by flash column chromatography (SiO2-PE80-100° C./EtOAc/CH3COOH=1:1:1%) to yield 3.6 mg (17%) of pure product.

Source