HCID 14820336, compound → [3-(Dimethoxymethyl)phenyl]-3-pyridinylmethanone

HRID 1088735Notes

Reaction equation

HRID 1088735 reaction equation
[CH3:1][O:2][CH:3]([O:18][CH3:19])[C:4]1[CH:5]=[C:6]([CH:10]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[OH:11])[CH:7]=[CH:8][CH:9]=1>[O-2].[Mn+4].[O-2].ClCCl>[CH3:1][O:2][CH:3]([O:18][CH3:19])[C:4]1[CH:5]=[C:6]([C:10]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[O:11])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 14820336HCID 14820336, compound

Product 1

HCID 14820340[3-(Dimethoxymethyl)phenyl]-3-pyridinylmethanoneYield 82%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 19 parts of α-[3-(dimethoxymethyl)phenyl]-3-pyridinemethanol, 36 parts of activated manganese(IV) oxide and 280 parts of dichloromethane was stirred over weekend at room temperature. The reaction mixture was filtered over silica gel and the filtrate was filtered again over diatomaceous earth and silica gel. The filtrate was evaporated and the residue was distilled in vacuo. The desired fraction was collected, yielding 15.7 parts (82%) of [3-(dimethoxymethyl)phenyl] (3-pyridinyl)methanone (intermediate 6).

Workup

  1. filtrationThe reaction mixture was filtered over silica gel
  2. filtrationthe filtrate was filtered again over diatomaceous earth and silica gel
  3. customThe filtrate was evaporated
  4. distillationthe residue was distilled in vacuo
  5. customThe desired fraction was collected

Sources & evidence

ORD record
ord-f728125741b24b51a0e13078ffe6afd9
Source dataset
uspto-grants-1990_10
Patent number
US04963573

Reaction notes

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