Réaction #2292356

Équation de réaction

triethylamine

DMSO

oxalyl chloride

compound 2

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-(benzyloxymethyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

→

(3aR,5R,6S,6aR)-6-(benzyloxy)-5-(benzyloxymethyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.WAITThe stirring was continued for 45 min at −78° C.
2. 2
   workup.STIRRINGThe reaction was stirred at −78° C. for 15 min
3. 3
   Autreafter which the ice-bath was removed
4. 4
   Températureto gradually warm over 45 min
5. 5
   workup.ADDITIONThe reaction was diluted with dichloromethane
6. 6
   Lavagethe organic phase was sequentially washed with 5% aqueous HCl solution, saturated aqueous NaHCO3 solution, brine
7. 7
   Séchagedried (Na2SO4)
8. 8
   Concentrationconcentrated under reduced pressure
9. 9
   Autreto provide 3 (2.2 g, crude), which
10. 10
    Autrewas used without any further purification

Mode opératoire

DMSO (1.65 mL, 23.6 mmol) was added drop-wise to a cold (−78° C.) solution of oxalyl chloride (1.05 mL, 12.0 mmol) in dichloromethane (50 mL). After stirring for 30 min, a solution of compound 2 (3 g, 7.5 mmol) in dichloromethane (25 mL) was added to the reaction. The stirring was continued for 45 min at −78° C., and triethylamine (3.5 mL, 25.0 mmol) was added to the reaction. The reaction was stirred at −78° C. for 15 min, after which the ice-bath was removed and the reaction was allowed to gradually warm over 45 min. The reaction was diluted with dichloromethane and the organic phase was sequentially washed with 5% aqueous HCl solution, saturated aqueous NaHCO3 solution, brine, dried (Na2SO4) and concentrated under reduced pressure to provide 3 (2.2 g, crude), which was used without any further purification. LC-MS (M+H)+=399.1

Source