Reacción #2075710

Ecuación de reacción

β-hydroxy ketone

3,4,5-trihydroxycyclohexanone

diisopropylethylamine

acetic anhydride

→

compound 9

Rendimiento 190.6%

dihydroxycyclohexenone

Rendimiento 190.6%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadothe solution was washed with saturated aqueous NaHCO3
2. 2
   Lavadothe NaHCO3 wash solution
3. 3
   Extracciónwas extracted with CH2Cl2 (4×40 ml)
4. 4
   SecadoThe organic layer was dried with MgSO4
5. 5
   Concentraciónconcentrated to dryness
6. 6
   OtroPurification by flash chromatography

Procedimiento

To a solution of the β-hydroxy ketone 8 (FIG. 6) (1.01 g, 3.85 mmol) in CH2Cl2 (10 mL) at 0° C. was added 4-(dimethylamino) pyridine (9.4 mg, 0.077 mmol), diisopropylethylamine (1.34 mL, 7.7 mmol) and acetic anhydride (0.44 mL, 4.6 mmol). After stirring at 0° C. for 6 hours, the solution was washed with saturated aqueous NaHCO3 and the NaHCO3 wash solution was extracted with CH2Cl2 (4×40 ml). The organic layer was dried with MgSO4 and concentrated to dryness. Purification by flash chromatography afforded compound 9 (FIG. 6) as a white solid (0.94 g, 100%). 1H NMR (CDCl3) δ 6.87 (dd, J=10.2, 1.8 Hz, 1H), 6.01 (dd, J=10.2, 2.4 Hz, 1H), 4.51 (dt, J=9.0, 2.1 Hz, 1H), 4.05 (m, 1H), 3.33 (s, 3H), 3.27 (s, 3H), 2.74 (dd, J=16.5, 13.2 Hz, 1H), 1.37 (s, 3H), 1.34 (s, 3H); 13C NMR (CDCl3) δ 196.8; 148.5; 130.1; 100.8; 99.7; 69.2; 8.0; 48.2; 48.1; 42.0; 17.7; 17.6.

Fuente