Propanal → HCID 68712580, compound

HRID 2113717Notes

Reaction equation

HRID 2113717 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1.[CH:9]([N-]C(C)C)([CH3:11])[CH3:10].[Li+].C(=[O:20])CC>O1CCCC1>[F:1][C:2]1[C:7]([CH2:10][CH:9]([OH:20])[CH3:11])=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1

Participants

5

Reactant 3

HCID 527PropanalHCID 739342,6-DifluoropyridineHCID 2724682Lithium diisopropylamide

Product 1

HCID 68712580HCID 68712580, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,6-difluoropyridine (5.0 mL, 0.0551 mol) in tetrahydrofuran (55 mL) was slowly added to a 1-necked flask containing lithium diisopropylamide (31 mL, 1.8 M in tetrahydrofuran) at −78° C. The reaction was stirred at this temperature for 30 minutes and then propionaldehyde (3.96 mL, 0.0551 mol) was added. After stirring at this temperature for an additional 30 minutes, the reaction was quenched by the addition of a saturated solution of ammonium chloride (20 mL). The product was extracted with diethylether, and purified by column chromatography using as eluent 10% ethyl acetate in hexanes to provide 6.7 g (70%) of 1-(2,6-difluoropyridin-3-yl)propan-2-ol.

Workup

  1. stirringAfter stirring at this temperature for an additional 30 minutes
  2. customthe reaction was quenched by the addition of a saturated solution of ammonium chloride (20 mL)
  3. extractionThe product was extracted with diethylether
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-2a23ed646b164e4d9221991637d66ae2
Source dataset
uspto-grants-2008_10
Patent number
US07432266B2

Reaction notes

Loading…