2-Bromopyridine → HCID 14098122, compound

HRID 2398099Notes

Reaction equation

HRID 2398099 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH:18]=[O:19].[NH4+].[OH-]>CCCCCC.CCOCC>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:18]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[OH:19])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]

Participants

7

Reactant 4

HCID 79732-BromopyridineHCID 8419VeratraldehydeHCID 14923Ammonium HydroxideHCID 178418339Butyllithium

Product 1

HCID 14098122HCID 14098122, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

A stirred solution of 187.5 ml of 1.6 M solution of butyllithium in hexane was cooled to -40° under nitrogen and 39.5 g (0.25 M) of 2-bromopyridine in 100 ml of ether added dropwise. The mixture was stirred 15 minutes at -40° and a solution of 41.5 g (0.25 M) of 3,4-dimethoxybenzaldehyde in 200 ml of ether added. After stirring at -15° for 45 minutes, the mixture was poured into 500 g ice/100 ml conc. HCl. The separated aqueous layer was made alkaline with conc. NH4OH, extracted with methylene chloride and the dried extract concentrated. The residual oil crystallized from benzene/hexane to give 3,4-dimethoxyphenyl-2-pyridyl carbinol, mp 92°-94°.

Workup

  1. stirringAfter stirring at -15° for 45 minutes
  2. extractionextracted with methylene chloride
  3. extractionthe dried extract
  4. concentrationconcentrated
  5. customThe residual oil crystallized from benzene/hexane

Sources & evidence

ORD record
ord-d8f9191f9ee04f949b028e659fb64558
Source dataset
uspto-grants-1977_05
Patent number
US04024158

Reaction notes

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