2-Pyridinecarboxaldehyde → HCID 15204724, compound

HRID 1769062Notes

Reaction equation

HRID 1769062 reaction equation
CO[C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH2:5][OH:6].C([Li])CCC.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH:24]=[O:25].[Cl-].[NH4+]>CCOCC.CCCCCC>[OH:6][CH2:5][C:4]1[CH:3]=[CH:10][CH:9]=[C:8]([O:11][CH3:12])[C:7]=1[CH:24]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=1)[OH:25]

Participants

7

Reactant 4

HCID 142732-PyridinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 1184952,5-Dimethoxybenzyl alcoholHCID 178418339Butyllithium

Product 1

HCID 15204724HCID 15204724, compoundYield 11.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
-20 °C

Procedure

To a mixture of 10 g (0.059 mol) of 2,5-dimethoxybenzyl alcohol in 250 ml of ether cooled to -20° C. was added in portions 12.75 ml (0.127 mol) of n-butyllithium (10M) in hexane over a 10 min period, and the reaction mixture was allowed to warm to room temperature and stirred 1 hr. The above reaction mixture was cooled to -20° C., 7.58 g (0.07 mol) of pyridine-2-carboxaldehyde was added to the mixture, and the resulting reaction mixture was allowed to warm to room temperature (a brown precipitate formed) and stirred for 1 hr. Ammonium chloride solution (60 ml) was added, the mixture was extracted with ethyl acetate, the combined organic layer was washed with brine, dried over sodium sulfate, and concentrated. The diol was purified by chromatography on silica eluting with ethyl acetate/hexane (9:1) to afford 1.7 g (10.5%) of 2-[(2',5'-dimethoxy-6'-hydroxymethyl)benzyl]pyridine (Formula XIII: R1 =R7 =H; R2 =2',5'(OCH3)2), as a white solid, m.p. 102°-104° C.

Workup

  1. temperatureto warm to room temperature
  2. customThe above reaction mixture
  3. temperaturewas cooled to -20° C.
  4. customthe resulting reaction mixture
  5. temperatureto warm to room temperature (a brown precipitate
  6. customformed) and
  7. stirringstirred for 1 hr
  8. extractionthe mixture was extracted with ethyl acetate
  9. washthe combined organic layer was washed with brine
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated
  12. customThe diol was purified by chromatography on silica eluting with ethyl acetate/hexane (9:1)

Sources & evidence

ORD record
ord-daefdf0deb82422da5b86890a377dc6c
Source dataset
uspto-grants-1995_01
Patent number
US05380729

Reaction notes

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