Reacción #40591

Ecuación de reacción

1

Salvinorin A

Na2CO3

→

8a

Rendimiento 77.0%

(2S,4aS,6aR,7R,9S,10aS,10bR)-9-(hydroxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester

Rendimiento 77.0%

Disolventes

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was removed under reduced pressure and CH2Cl2 (500 mL)
2. 2
   workup.ADDITIONwas added to the crude residue
3. 3
   ExtracciónThe organic extract
4. 4
   Lavadowas washed successively with 2N HCl (50 mL) and saturated NaCl (50 mL)
5. 5
   Secadodried (Na2SO4)
6. 6
   OtroThe solvent was removed under reduced pressure and MeOH (100 mL)
7. 7
   workup.ADDITIONwas added to the residue
8. 8
   FiltraciónThe resulting solid was collected by filtration
9. 9
   Otrodried

Procedimiento

A mixture of 1 (3.5 g, 8.0 mmol) and Na2CO3 (3.4 g, 32.2 mmol) in absolute MeOH (150 mL) was stirred at room temperature for 4 b. The solvent was removed under reduced pressure and CH2Cl2 (500 mL) was added to the crude residue. The organic extract was washed successively with 2N HCl (50 mL) and saturated NaCl (50 mL) and dried (Na2SO4). The solvent was removed under reduced pressure and MeOH (100 mL) was added to the residue. The resulting solid was collected by filtration and dried to afford 2.4 g (77%) of 8a as a white solid, mp 211-214° C. (Lit. 213-216° C.).

Fuente