Reaktion #163298

Reaktionsgleichung

NaOH

K2CO3

2-(1H-indazol-3-ylmethoxy)-2-methylpropanoic acid

benzoyl chloride

→

2-[(1-benzoyl-1H-indazol-3-yl)methoxy]-2-methylpropanoic acid

Ausbeute 22.7%

Lösungsmittel

acetone

water

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with diethyl ether (3×150 ml)
2. 2
   Extraktionextracted with diethyl ether (3×300 ml)
3. 3
   EinengenThe combined organic phases were concentrated under reduced pressure
4. 4
   Sonstigethe crude residue obtained
5. 5
   Sonstigewas purified by crystallization from a 1/1 hexane/ethyl acetate mixture

Vorschrift

To a solution of 2-(1H-indazol-3-ylmethoxy)-2-methylpropanoic acid (6 g; 0.026 mol) in acetone (50 ml) stirred at room temperature was added K2CO3 (6.8 g; 0.049 mol) and then, slowly, a solution of benzoyl chloride (5 ml; 0.043 mol) in acetone (30 ml). The mixture was stirred at room temperature for 24 hours and then poured into water (1 L). The solution was then brought to basic pH with 5N NaOH and washed with diethyl ether (3×150 ml). The alkaline phase was then acidified with concentrated HCl and extracted with diethyl ether (3×300 ml). The combined organic phases were concentrated under reduced pressure and the crude residue obtained was purified by crystallization from a 1/1 hexane/ethyl acetate mixture. 2 g of 2-[(1-benzoyl-1H-indazol-3-yl)methoxy]-2-methylpropanoic acid were obtained, m.p.=132-135° C.

Quelle