Water → HCID 59634074, compound

HRID 1615080Notes

Reaction equation

HRID 1615080 reaction equation
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1.O>CN(C=O)C>[N:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH2:16][CH2:15][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 2054424-(3-Chloropropyl)pyridine2×

Product 1

HCID 59634074HCID 59634074, compoundYield 465.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of NaH (0.4 g) in DMF (8 mL) was added diethyl malonate (0.16 g) at 0° C. The mixture was stirred at RT for 30 min. To the mixture was added a solution of 4-(3-chloropropyl)pyridine (1.2 g) prepared in (1) in DMF (4 mL). The reaction mixture was stirred at 80° C. for 10 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over Na2SO4. The solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (Developing solvent: hexane/ethyl acetate=1/1) to give the title compound (1.3 g, 60%).

Workup

  1. stirringThe reaction mixture was stirred at 80° C. for 10 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel chromatography (Developing solvent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-5af2d81df40545d7b27dfc3ea82bbe94
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

Loading…