3-Pyridinecarboxaldehyde → Dipyridin-3-ylmethanol

HRID 1360116Notes

Reaction equation

HRID 1360116 reaction equation
[Li]CCCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[CH:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1>CCOCC>[N:9]1[CH:10]=[CH:11][CH:12]=[C:7]([CH:13]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[OH:20])[CH:8]=1

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 122863-BromopyridineHCID 178418339Butyllithium

Product 1

HCID 11309949Dipyridin-3-ylmethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

n-BuLi (42 mL, 1.6M, 67 mmol) was added to a solution of 3-bromopyridine (5.9 mL, 9.74 g, 62 mmol) in ether (200 mL) at −78 C. The resulting yellow suspension was stirred for 1 h. A solution of nicotinaldehyde (5.3 mL, 6 g, 56 mmol) in ether (25 mL) was then added. After stirring for 0.5 h, the reaction mixture was allowed to warm gradually to 0 C. The reaction mixture was then quenched by addition of half saturated brine (100 mL). The resulting mixture was extracted once with ethyl acetate and once with chloroform. Drying (1:1 Na2SO4/K2CO3) and concentration gave dipyridin-3-ylmethanol as a very viscous orange oil which was used without further purification.

Workup

  1. stirringAfter stirring for 0.5 h
  2. temperatureto warm gradually to 0 C
  3. customThe reaction mixture was then quenched by addition of half saturated brine (100 mL)
  4. extractionThe resulting mixture was extracted once with ethyl acetate and once with chloroform
  5. customDrying
  6. concentration(1:1 Na2SO4/K2CO3) and concentration

Sources & evidence

ORD record
ord-49143ba9d6ec48de8eef3d6b31c48539
Source dataset
uspto-grants-2011_02
Patent number
US07879839B2

Reaction notes

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