HCID 22145868, compound → HCID 15453395, compound

HRID 1825408Notes

Reaction equation

HRID 1825408 reaction equation
[CH:1]1([O:6][C:7]2[C:12]([O:13][CH3:14])=[CH:11][N:10]=[C:9]([CH2:15][OH:16])[CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(OCC)C.ClCCl.[O-2].[O-2].[Mn+4]>[CH:1]1([O:6][C:7]2[C:12]([O:13][CH3:14])=[CH:11][N:10]=[C:9]([CH:15]=[O:16])[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 1

HCID 22145868HCID 22145868, compound

Product 1

HCID 15453395HCID 15453395, compoundYield 83.3%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Manganese dioxide (6.0 g) is added to a solution of 4-cyclopentyloxy-2-hydroxymethyl-5-methoxypyridine (2.0 g) in diethyl ether (80 mL) and dichloromethane (10 mL) and the mixture stirred at room temperature for 90 hours. After filtering the filter pad is washed with dichloromethane and the combined filtrate and washings are evaporated to give a white solid. The solid is dried under high vacuum to give 4-cyclopentyloxy-5-methoxypyridine-2-carboxaldehyde (1.65 g). [1Hnmr in D6-DMSO shifts relative to Me4Si:—1.55–1.79, 6H, m; 1.97, 2H, m; 3.96, 3H, s; 5.03, 1H, m; 7.45, 1H, s; 8.41, 1H, s; 9.83, 1H, s.].

Workup

  1. filtrationAfter filtering the filter pad
  2. washis washed with dichloromethane
  3. customthe combined filtrate and washings are evaporated
  4. customto give a white solid
  5. customThe solid is dried under high vacuum

Sources & evidence

ORD record
ord-e24e72730320497082ba0854d0a8c06e
Source dataset
uspto-grants-2006_05
Patent number
US07045660B2

Reaction notes

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