Reacción #40596

Ecuación de reacción

8a

(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

trichloroacetonitrile

→

21

Rendimiento 37.0%

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

Rendimiento 37.0%

Disolventes

dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe reaction mixture was then washed with saturated NaHCO3 (10 mL) and H2O (10 mL)
2. 2
   Secadodried (Na2SO4)
3. 3
   OtroThe solvent was removed under reduced pressure
4. 4
   Otroto give a crude oil
5. 5
   OtroThe oil was purified by column chromatography (eluent: ethyl acetate/n-hexanes)

Procedimiento

A solution of 8a (0.05 g, 0.13 mmol), trichloroacetonitrile (0.1 mL, 1.0 mmol), 1,8-Diazobicylo[5.4.0]undec-7-ene (0.05 mL, 0.3 mmol) in dichloroethane (20 mL) was stirred at 0° C. for 24 h. The reaction mixture was then washed with saturated NaHCO3 (10 mL) and H2O (10 mL) and dried (Na2SO4). The solvent was removed under reduced pressure to give a crude oil. The oil was purified by column chromatography (eluent: ethyl acetate/n-hexanes) to afford 21 (0.02 g, 37%) as a white solid, mp 120-123° C.; 1H NMR (CDCl3): δ 1.18 (s, 3H); 1.50 (s, 3H); 1.52-1.76 (m, 4H); 1.85 (dd, Ja=2.6, Jb=10.1, 1H); 2.10 (dd, Ja=2.9, Jb=11.6, 1H); 2.20 (m, 1H); 2.24 (s, 1H); 2.35-2.58 (m, 3H); 2.80 (dd, Ja=4.1, Jb=12.5, 1H); 3.75 (s, 3H); 5.34 (dd, Ja=7.7, Jb=12.2, 1H); 6.40 (dd, Ja=0.9, Jb=1.5, 1H); 7.41 (dd, 1H, 1.5, 1.5, 1H); 7.43 (dd, Ja=0.9, Jb=1.5, 1H); 8.38 (s, 1H).

Fuente