HCID 22145868, compound → HCID 15453395, compound

HRID 993299Notes

Reaction equation

HRID 993299 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-fb612f239788409da861317dd65e4a29
Source dataset
uspto-grants-2002_10
Patent number
US06472412B1

Reaction notes

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