Réaction #2059

Équation de réaction

2-[2,4-dichloro-5-(2-propynyloxy)-phenyl]-2,4-dihydro-5-(3,4-epoxybutyl)-3H-1,2,4-triazol-3-one

potassium carbonate

→

title product

Rendement 36.8%

5,6,7,8-tetrahydro-2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-6-hydroxy- 1,2,4-triazolo[4.3-α]pyridin-3(2H)-one

Rendement 36.8%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   Températurewas warmed
2. 2
   Températureat reflux for 2h
3. 3
   Filtrationfiltered
4. 4
   AutreThe filtrate was evaporated in vacuo
5. 5
   AutreThe crude product was purified by flash chromatography over silica gel
6. 6
   Lavageeluting with a 95:5 v
7. 7
   workup.ADDITIONv mixture of dichloromethane and methanol

Mode opératoire

A mixture of 500 mg (1.41 mmol) of 2-[2,4-dichloro-5-(2-propynyloxy)-phenyl]-2,4-dihydro-5-(3,4-epoxybutyl)-3H-1,2,4-triazol-3-one and 563 mg (4.08 mmol) of potassium carbonate in 20 mL of acetonitrile was warmed at reflux for 2h. The mixture was cooled to room temperature and filtered. The filtrate was evaporated in vacuo. The crude product was purified by flash chromatography over silica gel, eluting with a 95:5 v:v mixture of dichloromethane and methanol to give 184 mg of the title product of Step 4 as a pale yellow foam, 1H NMR (CDCl3, 400 MHz) δ 7.5 (s,1H), 7.15 (s,1H), 4.8 (s,2H), 4.45 (broad t,1H), 3.8 (m,2H), 3.0 (m,1H), 2.8 (m,1H), 2.6 (s,1H), 2.2 (s,1H), 2.15 (m,1H), 1.95 (m,1H).

Source