Pyridine → HCID 86587934, compound

HRID 25702Notes

Reaction equation

HRID 25702 reaction equation
N1C=CC=CC=1.[CH3:7][O:8][CH:9]1[C@@H:13]2[O:14][C:15]([CH3:18])([CH3:17])[O:16][C@@H:12]2[C@@H:11]([CH2:19][OH:20])[O:10]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.[O-2].[Cr+3].[O-2].[O-2].[Cr+3]>[CH3:7][O:8][CH:9]1[C@@H:13]2[O:14][C:15]([CH3:18])([CH3:17])[O:16][C@@H:12]2[C@H:11]([CH:19]=[O:20])[O:10]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 11447040Methyl-2,3-O-isopropylidene-D-ribofuranoside

Product 1

HCID 86587934HCID 86587934, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 165971Chromium oxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

By using the literature known procedure (Barrett, A. G. M.; Lebold, S. A., J. Org. Chem., 1990, 55, 3853), to a solution of dry pyridine (48.5 ml) in anhydrous methylene chloride (700 ml) was added chromium oxide (30 g, 0.3 mole) portionwise under nitrogen. During this procedure the reaction mixture was kept at room temperature by occasional cooling with an ice-water bath. To this dark red solution was added a solution of [(3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methanol (5 g, 24.48 mmole, obtained from Reference Example 35) in methylene chloride (100 ml) under nitrogen. The resulting mixture was stirred at room temperature for 30 min, and poured into a cold aqueous solution of saturated sodium bicarbonate. The organic layer was separated and the aqueous layer was extracted with methylene chloride. The combined extracts were washed well with saturated sodium chloride solution until the color of the organic layer turned yellow, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was dissolved in benzene, and the solvent was removed in vacuo. This procedure was repeated several more times, to give [(3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbaldehyde (2.8 g, 56.6%) as a yellow amorphous solid. The aldehyde was dissolved in benzene and stored in the freezer under argon.

Workup

  1. customwas kept at room temperature
  2. temperatureby occasional cooling with an ice-water bath
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with methylene chloride
  5. washThe combined extracts were washed well with saturated sodium chloride solution until the color of the organic layer
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. dissolutionThe residue was dissolved in benzene
  10. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0633819b126141fcb506cb8df6d4a192
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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