Реакция #567340

Уравнение реакции

bicyclo-[2.2.2]octane-1,4-dicarboxylic acid monomethyl ester

Bicyclo-[2.2.2]octane-1,4-dicarboxylic acid monomethyl ester

Bicyclo-[2.2.2]octane-1,4-dicarboxylic acid monomethyl ester

dimethylformamide

Bromocresol green

oxalyl chloride

→

title compound

4-Chlorocarbonylbicyclo[2.2.2]octane-1-carboxylic acid methyl ester

Растворители

dichloromethane methanol

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   workup.ADDITIONthe resulting mixture is added to the mixture
2. 2
   ДругоеThe solvent is removed under reduced pressure at 40 to 45°
3. 3
   workup.ADDITIONdichloromethane (5 vol) is added
4. 4
   workup.STIRRINGstirred for 5 to 15 min
5. 5
   Другоеremoved under reduced pressure at 40 to 45°
6. 6
   workup.ADDITIONby adding dichloromethane (5 vol)
7. 7
   workup.STIRRINGstirring for 5 to 15 min
8. 8
   Другоеremoving under reduced pressure at 40 to 45°
9. 9
   workup.ADDITIONAcetonitrile (6.25 vol) is then added

Методика

Bicyclo-[2.2.2]octane-1,4-dicarboxylic acid monomethyl ester (IV, Example 81, 1 wt) is dissolved in dichloromethane (6.25 vol) and dimethylformamide (0.025 vol) is added. Concomitantly oxalyl chloride (0.5125 vol) is dissolved in dichloromethane (0.625 vol) and the resulting mixture is added to the mixture containing the bicyclo-[2.2.2]octane-1,4-dicarboxylic acid monomethyl ester (IV) at between 12 to 17° C., taking care for gas evolution. The mixture is stirred at 15 to 25° for 2 to 4 hours which is monitored by (TLC; dichloromethane/methanol: 9/1, visualization Bromocresol green). The solvent is removed under reduced pressure at 40 to 45°, dichloromethane (5 vol) is added, stirred for 5 to 15 min and removed under reduced pressure at 40 to 45°. The process is repeated by adding dichloromethane (5 vol), stirring for 5 to 15 min and removing under reduced pressure at 40 to 45°. Acetonitrile (6.25 vol) is then added to give the title compound in solution.

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