(2-Phenyl-2H,4H-[1,3]dioxino[5,4-b]pyridin-6-yl)methanol → 2-Phenyl-2H,4H-[1,3]dioxino[5,4-b]pyridine-6-carbaldehyde

HRID 437393Notes

Reaction equation

HRID 437393 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:7][CH:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:9][CH2:10][C:11]=2[N:12]=1>[O-2].[O-2].[Mn+4].C1C=CC=CC=1>[CH:2]([C:3]1[CH:4]=[CH:5][C:6]2[O:7][CH:8]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[O:9][CH2:10][C:11]=2[N:12]=1)=[O:1]

Participants

4

Reactant 1

HCID 428642(2-Phenyl-2H,4H-[1,3]dioxino[5,4-b]pyridin-6-yl)methanol

Product 1

HCID 137484012-Phenyl-2H,4H-[1,3]dioxino[5,4-b]pyridine-6-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 241BenzeneSolvent

Procedure

To a suspension of 38.8 g. (0.4 mole) of activated manganese dioxide in 400 ml. of benzene is added 48.6 g. (0.2 mole) of 6-hydroxymethyl-2-phenyl-4H-pyrido[3,2-d]-1,3-dioxin in 250 ml. of the same solvent, and the mixture stirred at the reflux temperature overnight. The mixture is filtered while hot (50° C.) and the filtrate concentrated under vacuum to an oily foam, 49.7 g. The intermediate product is purified by chromatographing on a silica gel column (1 kg. 60-200 mesh silica gel; 8 cm × 75 cm column), the product being eluted with ethyl acetate. The eluates are combined and evaporated to dryness, 11.75 g., m.p. 110°-114° C.

Workup

  1. additionTo a suspension of 38.8 g
  2. filtrationThe mixture is filtered while hot (50° C.)
  3. concentrationthe filtrate concentrated under vacuum to an oily foam, 49.7 g
  4. customThe intermediate product is purified by chromatographing on a silica gel column (1 kg. 60-200 mesh silica gel; 8 cm × 75 cm column)
  5. washthe product being eluted with ethyl acetate
  6. customevaporated to dryness, 11.75 g

Sources & evidence

ORD record
ord-4c02b21836644388b2d43705baab7797
Source dataset
uspto-grants-1977_06
Patent number
US04031108

Reaction notes

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