Propanal → 1055306-54-1

HRID 218515Notes

Reaction equation

HRID 218515 reaction equation
[Li+].CC([N-]C(C)C)C.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[CH:16](=[O:19])[CH2:17][CH3:18].[Cl-].[NH4+]>C1COCC1>[F:9][C:10]1[C:15]([CH:16]([OH:19])[CH2:17][CH3:18])=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

6

Reactant 4

HCID 527PropanalHCID 97462-FluoropyridineHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamide

Product 1

HCID 595867221055306-54-1

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A freshly prepared LDA solution (68.0 mmol) in 500 ml of THF is cooled to −75° C., and 6.00 g (61.8 mmol) of 2-fluoropyridine are added. The mixture is left to stir at this temperature for 2 h, in the course of which a suspension forms. Thereafter, 4.31 g (74.2 mmol) of propanal are added, in the course of which the internal temperature rises to −45° C. After 2 h, the mixture is allowed to come to RT, poured onto saturated ammonium chloride solution and extracted three times with tert-butyl methyl ether. The combined organic phases are washed with sodium chloride solution, dried over sodium sulfate and concentrated. They are purified by chromatography on silica gel (eluent: dichloromethane, then dichloromethane/methanol=25:1). This affords 8.00 g (76% of theory) of the title compound.

Workup

  1. waitThe mixture is left
  2. customrises to −45° C
  3. waitAfter 2 h
  4. customto come to RT
  5. extractionextracted three times with tert-butyl methyl ether
  6. washThe combined organic phases are washed with sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThey are purified by chromatography on silica gel (eluent

Sources & evidence

ORD record
ord-4529857d3d6849c3b161da401624cc93
Source dataset
uspto-grants-2012_06
Patent number
US08198267B2

Reaction notes

Loading…