Hydrochloric Acid → Methyl 2-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-3-oxoheptanoate

HRID 2048613Notes

Reaction equation

HRID 2048613 reaction equation
[H-].[Na+].[O:3]=[C:4]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:5][C:6]([O:8][CH3:9])=[O:7].Cl[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=2[C:24]#[N:25])=[N:20][CH:21]=1.Cl>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:24]([C:23]1[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=1[C:19]1[N:20]=[CH:21][C:16]([CH2:15][CH:5]([C:4](=[O:3])[CH2:10][CH2:11][CH2:12][CH3:13])[C:6]([O:8][CH3:9])=[O:7])=[CH:17][CH:18]=1)#[N:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 546075Methyl 3-oxoheptanoateHCID 99913952-(5-(Chloromethyl)pyridin-2-yl)benzonitrile

Product 1

HCID 67008908Methyl 2-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-3-oxoheptanoateYield 12.9%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 60% sodium hydride in oil (3.27 g) and tetrahydrofuran (50 mL) was added dropwise a mixture of methyl 3-oxoheptanoate (16.18 g) in tetrahydrofuran (50 mL) at 0° C., and the mixture was stirred at room temperature for 30 min. Then, 2-[5-(chloromethyl)pyridin-2-yl]benzonitrile (4.45 g) and tetrabutylammonium iodide (2.27 g) were added, and the mixture was stirred at room temperature overnight. The reaction mixture was poured into 1 M hydrochloric acid (70 mL), and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a yellow oil (0.88 g, 12%).

Workup

  1. additionwas added dropwise
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c66987ca62404bd98a7fb1db4c4ce382
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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