6-Butoxy-2-hydroxymethylpyridine → 6-Butoxypyridine-2-carbaldehyde

HRID 912700Notes

Reaction equation

HRID 912700 reaction equation
[CH2:1]([O:5][C:6]1[N:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:5][C:6]1[N:11]=[C:10]([CH:12]=[O:13])[CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 197561166-Butoxy-2-hydroxymethylpyridine

Product 1

HCID 108450736-Butoxypyridine-2-carbaldehydeYield 84%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Activated manganese dioxide (2.40 g, 27.6 mmol) was added to a solution of (6-butoxy-pyridin-2-yl)methanol (0.52 g, 2.85 mmol, obtained from Example 17(c)) in anhydrous dichloromethane (5 mL). The resulting solution was heated to reflux for 2 h and then cooled to r.t. and 50 mL of dichloromethane added. The black solid was removed by filtration through silica gel and washed with dichloromethane. The combined filtrate was concentrated in vacuo providing the title compound (0.43 mg, 84%) as a light yellow oil.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 2 h
  3. customThe black solid was removed by filtration through silica gel
  4. washwashed with dichloromethane
  5. concentrationThe combined filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9c4665e5dd6149efb98ef77713b1b34c
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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