(3-(Benzyloxy)-6-methylpyridin-2-yl)methanol → 3-(Benzyloxy)-6-methylpicolinaldehyde

HRID 490279Notes

Reaction equation

HRID 490279 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:16][OH:17])=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.O=[Mn]=O>[CH3:15][C:12]1[N:11]=[C:10]([CH:16]=[O:17])[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 22711808(3-(Benzyloxy)-6-methylpyridin-2-yl)methanol

Product 1

HCID 227117753-(Benzyloxy)-6-methylpicolinaldehydeYield 94%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(benzyloxy)-6-methyl-2-pyridinemethanol (0.0314 mol) and MnO2 (29.52 g) in CH2Cl2 (100 ml) was stirred at room temperature overnight and then purified over silica gel on a glass filter (eluent: CH2Cl2 100%). The pure fractions were collected and the solvent was evaporated, yielding 6.71 g of 6-methyl-3-(phenylmethoxy)-2-pyridinecarboxaldehyde (94%) (interm. 6).

Workup

  1. custompurified over silica gel on a glass
  2. filtrationfilter (eluent: CH2Cl2 100%)
  3. customThe pure fractions were collected
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-436eb99919514c43aead883d56785d27
Source dataset
uspto-grants-2009_05
Patent number
US07528149B2

Reaction notes

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