Reaction #1346

Reaction equation

ammonium chloride

4-(2-chlorophenyl)-2-(2,3-dihydroxypropoxymethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester

sodium periodate

→

title compound

Yield 97.9%

4-(2-Chlorophenyl)-2-methyl-6-(2-oxo-ethoxymethyl)-1,4-dihydro-3,5-pyridinedicarboxylic acid 5-ethyl 3-methyl ester

Yield 97.9%

Solvents

methanol

water

Conditions

Workup

1. 1
   OtherVolatile materials were removed under reduced pressure
2. 2
   workup.ADDITIONethyl acetate (200 mL) and water (100 mL) were added
3. 3
   OtherThe organic layer was separated
4. 4
   Extractionthe aqueous layer was twice extracted with ethyl acetate (50 mL)
5. 5
   WashThe combined organic fractions was washed with brine
6. 6
   Dryingdried (sodium sulfate)
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated in vacuo

Procedure

To an ice-cooled solution of 4-(2-chlorophenyl)-2-(2,3-dihydroxypropoxymethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester (IC, 13.0 g) in methanol (150 mL) was added a solution of sodium periodate (7.6 g) dissolved in water (100 mL) dropwise over 15 min. After stirring for 10 min, a saturated solution of ammonium chloride (25 mL) was added. Volatile materials were removed under reduced pressure, then ethyl acetate (200 mL) and water (100 mL) were added. The organic layer was separated and the aqueous layer was twice extracted with ethyl acetate (50 mL). The combined organic fractions was washed with brine, dried (sodium sulfate), filtered and concentrated in vacuo to afford the title compound (11.8 g). Thin layer chromatography and proton NMR spectrum showed the crude title compound (ID) was sufficiently pure.

Source