2-Bromopyridine → alpha-(3,4-Dimethoxy-5-nitrophenyl)-2-pyridinemethanol

HRID 274499Notes

Reaction equation

HRID 274499 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([N+:25]([O-:27])=[O:26])[C:22]=1[O:23][CH3:24])[CH:18]=[O:19]>O1CCCC1>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:18]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[OH:19])[CH:20]=[C:21]([N+:25]([O-:27])=[O:26])[C:22]=1[O:23][CH3:24]

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 108675653,4-Dimethoxy-5-nitrobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 21459111alpha-(3,4-Dimethoxy-5-nitrophenyl)-2-pyridinemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.76 ml of 2-bromopyridine dissolved in 30 ml of absolute tetrahydrofuran are treated -60° within 30 minutes with 19.2 ml of 1.6M n-butyl lithium solution (in hexane), whereupon the mixture is stirred at -60° for 30 minutes. 6.0 g of 3,4-dimethoxy-5-nitrobenzaldehyde dissolved in 50 ml of tetrahydrofuran are then added dropwise thereto at -40° within 30 minutes. The reaction mixture is warmed to 0° within 2 hours, poured into ice-water and extracted with ethyl acetate. The combined extracts are dried over sodium sulfate and evaporated, and the residue is chromatographed on 200 g of silica gel with ethyl acetate. There is obtained α-(3,4-dimethoxy-5-nitrophenyl)-2-pyridinemethanol as a brown oil.

Workup

  1. additionare then added dropwise
  2. waitat -40° within 30 minutes
  3. temperatureThe reaction mixture is warmed to 0° within 2 hours
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined extracts are dried over sodium sulfate
  6. customevaporated
  7. customthe residue is chromatographed on 200 g of silica gel with ethyl acetate

Sources & evidence

ORD record
ord-ba36c3f25f13485896f19f9b206a90c2
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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