Dimethylformamide → 6-(Benzyloxy)nicotinaldehyde

HRID 1353574Notes

Reaction equation

HRID 1353574 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[CH:23]=[O:24].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]1[N:10]=[CH:11][C:12]([CH:23]=[O:24])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 111081912-Benzyloxy-5-bromopyridineHCID 178418339Butyllithium

Product 1

HCID 211022056-(Benzyloxy)nicotinaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-benzyloxy-5-bromo-pyridine (1.64 g, 6.2 mmol) in tetrahydrofuran (25 mL, −78° C.) was added n-butyllithium (2.5 M in hexane, 2.61 mL, 1.05 equiv). After 1 h at −78° C., dimethylformamide (0.97 mL, 2 equiv) was added and the mixture stirred for 30 min. The reaction was quickly poured into a stirred solution of 5% aqueous sodium bicarbonate (50 mL) and extracted with diethyl ether (3×). The ethereal was washed with brine, dried over magnesium sulfate, and concentrated to give 1.16 g (quant.) which was used without purification. Mass spec.: 186.34 (MH)+.

Workup

  1. extractionextracted with diethyl ether (3×)
  2. washThe ethereal was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give 1.16 g (quant.) which
  6. customwas used without purification

Sources & evidence

ORD record
ord-6603b27f03e44dd9a18ad6371a355ba8
Source dataset
uspto-grants-2007_05
Patent number
US07220862B2

Reaction notes

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