Reacción #612694

Ecuación de reacción

carbon monoxide

Xantphos

triethylamine

2,2-dichloro-1-((4S,5R)-4-(fluoromethyl)-5-(4-iodophenyl)-2,2-dimethyloxazolidin-3-yl)ethanone

→

title compound

Methyl 4-((4S,5R)-3-(2,2-dichloroacetyl)-4-(fluoromethyl)-2,2-dimethyloxazolidin-5-yl)benzoate

Disolventes

methanol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroCarbon monoxide gas is bubbled through the solution
2. 2
   Temperaturacooled to room temperature
3. 3
   Extracciónextracted with ethylacetate
4. 4
   Secadodried over Na2SO4
5. 5
   Concentraciónconcentrated under vacuum
6. 6
   OtroThe residue is chromatographed on silica gel eluting from 100% hexanes to 50:50 ethylacetate

Procedimiento

To a flask containing 2,2-dichloro-1-((4S,5R)-4-(fluoromethyl)-5-(4-iodophenyl)-2,2-dimethyloxazolidin-3-yl)ethanone (2.0 g, 4.48 mmol) is added triethylamine (5 mL) and methanol (5 mL). Carbon monoxide gas is bubbled through the solution while stirring for 30 min. Pd(OAc)2 (51 mg, 0.22 mmol) and Xantphos (132 mg, 0.22 mmol) are next added and a balloon containing carbon monoxide is secured to the flask outlet. The reaction is heated for 2 hours at 60° C. and then cooled to room temperature. Next, the reaction is diluted with water, extracted with ethylacetate, dried over Na2SO4, and concentrated under vacuum. The residue is chromatographed on silica gel eluting from 100% hexanes to 50:50 ethylacetate:hexanes to afford the title compound (1.11 g): 1H NMR (400 MHz, CDCl3) 8.10 (d, 2H, J=8.0 Hz), 7.55 (d, 2H, J=8.0 Hz), 6.34 (m, 1H), 5.30-4.42 (m, 4H), 3.95 (s, 3H), 1.97-1.53 (m, 6H). m/z (Cl) 320 [M-(CH3)2CO].

Fuente