Reacción #95455

Ecuación de reacción

ethyl 4-formyl-1,2,5-trimethylpyrrole-3-carboxylate

sodium borohydride

water

→

ethyl 4-(hydroxymethyl)-1,2,5-trimethylpyrrole-3-carboxylate

Disolventes

methanol

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawhile maintaining the reaction temperature below 50° C.
2. 2
   workup.ADDITIONafter total addition the reaction mixture
3. 3
   Extracciónthe reaction mixture saturated with potassium carbonate and extracted with ether
4. 4
   SecadoThe combined ether extracts are dried
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   Otroleaving a yellow solid which
7. 7
   Otrois recrystallized from cyclohexane

Procedimiento

To a suspension of 10.9 g of ethyl 4-formyl-1,2,5-trimethylpyrrole-3-carboxylate in 40 ml of methanol is added dropwise under nitrogen 5.6 g of sodium borohydride in methanol while maintaining the reaction temperature below 50° C. after total addition the reaction mixture is stirred at ambient temperature for 4 hours, then 90 ml of water introduced and the reaction mixture saturated with potassium carbonate and extracted with ether. The combined ether extracts are dried and concentrated in vacuo leaving a yellow solid which is recrystallized from cyclohexane to give ethyl 4-(hydroxymethyl)-1,2,5-trimethylpyrrole-3-carboxylate, mp 184°-186° C.

Fuente