反应详情

To a suspension of 60% NaH (2.7 g; 0.07 mol) in toluene (200 ml) was added 1-benzyl-3-hydroxymethylindazole (10 g; 0.07 mol). The mixture was brought to the boiling point and left stirring at reflux for 1 hour. 4-Methoxybenzyl chloride (14 g; 0.09 mol) was then added. The mixture was then stirred at reflux for 4 hours. The reaction was stopped by cooling the mixture to room temperature and adding water (50 ml). The organic phase was separated out and washed, respectively, with 2N HCl (50 ml) and water (5×50 ml). The solvent was evaporated off under reduced pressure. The crude residue thus obtained was purified by flash chromatography on silica gel, using as eluent a 3/2 hexane/ethyl acetate mixture. The product obtained was crystallized from a 5/1 hexane/ethyl acetate mixture to give 5.1 g of [1-(4-methoxybenzyl)-1H-indazol-3-yl]methanol with a melting point of 95-97° C.

1. waitleft
2. temperatureat reflux for 1 hour
3. stirringThe mixture was then stirred
4. temperatureat reflux for 4 hours
5. customThe organic phase was separated out and
6. washwashed
7. customThe solvent was evaporated off under reduced pressure
8. customThe crude residue thus obtained
9. customwas purified by flash chromatography on silica gel
10. customThe product obtained
11. customwas crystallized from a 5/1 hexane/ethyl acetate mixture