Reacción #414483

Ecuación de reacción

sodium boron hydride

hydrochloric acid

sodium hydrogen sulfite

sodium chloride

sodium periodate

geniposide

→

genipin

Rendimiento 73.8%

Disolventes

ether

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction mixture was further stirred at room temperature for two hours
2. 2
   workup.STIRRINGthe reaction mixture was stirred at room temperature for four hours
3. 3
   workup.STIRRINGthe reaction mixture was stirred
4. 4
   Otroto thereby separate an ether layer
5. 5
   OtroAfter the ether layer was separated
6. 6
   Otrodried
7. 7
   workup.DISTILLATIONether was distilled off
8. 8
   Otroa yellow solid was obtained
9. 9
   OtroThe solid was further recrystallized from methanol and ether

Procedimiento

First, 100 g of geniposide was dissolved in 650 ml of water. After 115 g of sodium periodate was added to the solution, the reaction mixture was stirred at room temperature for two hours. After 41 g of sodium boron hydride was further added, the reaction mixture was further stirred at room temperature for two hours. Subsequently, a 6N aqueous hydrochloric acid solution and ether were added, the reaction mixture was stirred at room temperature for four hours After the addition of sodium hydrogen sulfite and sodium chloride, the reaction mixture was stirred to thereby separate an ether layer. After the ether layer was separated and dried, ether was distilled off, and a yellow solid was obtained. The solid was further recrystallized from methanol and ether to yield 43 g of genipin.

Fuente