Dimethylformamide → HCID 67382816, compound

HRID 2176893Notes

Reaction equation

HRID 2176893 reaction equation
[CH3:1][CH2:2][CH:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].Cl.Cl[CH2:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1.[CH3:24]N(C=O)C>>[N:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH:2]([CH:3]([C:4]([O:6][CH2:7][CH3:24])=[O:5])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:1])=[CH:19][CH:20]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 745704-(Chloromethyl)pyridinium chlorideHCID 5088009HCID 5088009, compound

Product 1

HCID 67382816HCID 67382816, compoundYield 68.1%

Procedure

To a suspension of diethyl methyl malonate (2.41 g, 13.9 mmol) in DMF (50 ml) at 0° C. was added sodium hydride (1.66 g, 41.6 mmol, 60%), followed by adding the compound 4-chloromethylpyridine hydrochloride (2.50 g, 15.2 mmol) and stirred for 16 h at room temperature. The reaction mixture was quenched by acetic acid and the product was extracted with ethyl acetate. The combined ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 2.50 g (68.1%) of diethyl 2-(1-(pyridin-4-yl)propan-2-yl)malonate as pale brown oil.

Workup

  1. customThe reaction mixture was quenched by acetic acid
  2. extractionthe product was extracted with ethyl acetate
  3. washThe combined ethyl acetate layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8487880c3f544bad81434e22fefe94a7
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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