Reaction #44010

Reaction equation

Compound 78

(5-(4-chlorophenylsulfonyl)-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridin-4-yl)methanol

NaHCO3

Dess-Martin periodinane

→

79

Yield 81.9%

5-(4-chlorophenylsulfonyl)-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-4-carbaldehyde

Yield 81.9%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   Otherwas quenched with sat. NaHCO3 (10 mL) and 10%
2. 2
   workup.STIRRINGThe mixture was stirred at room temperature for 30 minutes
3. 3
   ExtractionThe reaction mixture was extracted with CH2Cl2
4. 4
   Washthe combined organic layers were washed with brine
5. 5
   DryingThe organic layer was dried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo

Procedure

Compound 78 (0.50 g, 1.5 mmol) was dissolved in CH2Cl2 (5 mL). NaHCO3 (0.3 g, 3.6 mmol) was added, followed by Dess-Martin periodinane (0.78 g, 1.8 mmol). The reaction stirred at room temperature for two hours and was quenched with sat. NaHCO3 (10 mL) and 10% w/v sodium bisulfite (10 mL). The mixture was stirred at room temperature for 30 minutes. The reaction mixture was extracted with CH2Cl2 and the combined organic layers were washed with brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to yield 0.4 g of 79 as a white solid that was used without further purification.

Source