Acetone → HCID 59539022, compound

HRID 2039774Notes

Reaction equation

HRID 2039774 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[CH2:14]([O:16][C:17]([C:19]1[CH:29]=[C:22]2[C:23]([CH2:27][OH:28])=[CH:24][CH:25]=[CH:26][N:21]2[N:20]=1)=[O:18])[CH3:15].CC(C)=O>C(O)(C)C>[CH3:15][CH2:14][O:16][C:17]([C:19]1[CH:29]=[C:22]2[C:23]([C:27]([OH:3])=[O:28])=[CH:24][CH:25]=[CH:26][N:21]2[N:20]=1)=[O:18]

Participants

5

Reactant 3

HCID 180AcetoneHCID 595389604-Hydroxymethylpyrazolo[1,5-a]pyridine-2-carboxylic acid ethyl esterHCID 131709961Jones' reagent

Product 1

HCID 59539022HCID 59539022, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A 2.65 M solution of the Jones reagent (28 mL) is added dropwise over 40 min to a solution of 4-hydroxymethylpyrazolo[1,5-a]pyridine-2-carboxylic acid ethyl ester (5.30 g, 24.1 mmol) and acetone (240 mL) under air cooled by a water bath. After 20 min, isopropanol (3 mL) is added dropwise. After stirring for 30 min, the blue-green mixture is filtered (acetone rinse). The organics are concentrated under reduced pressure. The residue is dissolved in water. Et2O is added and the mixture is stirred for 15 min. The resulting solid is collected by filtration. The filtrate is dried to afford the title compound as a tan solid. LC-MS m/z (M+Na+): 257.02§.

Workup

  1. temperaturecooled by a water bath
  2. filtrationthe blue-green mixture is filtered
  3. wash(acetone rinse)
  4. concentrationThe organics are concentrated under reduced pressure
  5. dissolutionThe residue is dissolved in water
  6. additionEt2O is added
  7. stirringthe mixture is stirred for 15 min
  8. filtrationThe resulting solid is collected by filtration
  9. customThe filtrate is dried

Sources & evidence

ORD record
ord-222cfdd8aa1c4e9ab565590267aa5232
Source dataset
uspto-grants-2013_11
Patent number
US08580812B2

Reaction notes

Loading…