Diethyl Ether → alpha-[2-(Dimethoxymethyl)phenyl]-3-pyridinemethanol

HRID 1646680Notes

Reaction equation

HRID 1646680 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:11][CH3:12])[O:9][CH3:10].O(CC)CC.C([Li])CCC.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]=[O:30])[CH:24]=1>CCCCCC>[CH3:10][O:9][CH:8]([O:11][CH3:12])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:29]([C:25]1[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=1)[OH:30]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 103713-PyridinecarboxaldehydeHCID 111489431-Bromo-2-(dimethoxymethyl)benzeneHCID 178418339Butyllithium

Product 1

HCID 14820335alpha-[2-(Dimethoxymethyl)phenyl]-3-pyridinemethanolYield 99.9%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a stirred and cooled (-78° C.) mixture of 50 parts of 1-bromo-2-(dimethoxymethyl)benzene and 245 parts of 1,1'-oxybisethane were added dropwise 59 parts of a 1-butyllithium solution 2.5M in hexane. Upon complete addition, stirring was continued for 10 minutes at room temperature. A solution of 23.1 parts of 3-pyridinecarboxaldehyde in 42 parts of 1,1'-oxybisethane was added dropwise to the reaction mixture. Upon completion, the mixture was allowed to reach room temperature. The mixture was taken up in ice water and the product was extracted with 1,1'-oxybisethane. The extract was dried, filtered and evaporated, yielding 56 parts (99.9%) of α-[2-(dimethoxymethyl)phenyl]-3-pyridinemethanol as a residue (intermediate 1).

Workup

  1. temperaturecooled
  2. additionUpon complete addition
  3. stirringstirring
  4. customto reach room temperature
  5. extractionthe product was extracted with 1,1'-oxybisethane
  6. customThe extract was dried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-9dbc941ac7174f71aedb29f0e24bd968
Source dataset
uspto-grants-1993_01
Patent number
US05180832

Reaction notes

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