Dimethylformamide → HCID 67382967, compound

HRID 1896263Notes

Reaction equation

HRID 1896263 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:19]=[N:20][CH:21]=[CH:22][CH:23]=1.[CH3:24]N(C=O)C>>[N:20]1[CH:21]=[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]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 24758Sodium hydrideHCID 5088009HCID 5088009, compound

Product 1

HCID 67382967HCID 67382967, compoundYield 91.2%

Procedure

To a suspension of diethyl methyl malonate (1.80 g, 10.2 mmol) in DMF (25 ml) at 0° C. was added sodium hydride (1.25 g, 31.0 mmol, 60%), followed by 3-(chloromethyl)pyridine hydrochloride (2.00 g, 12.2 mmol) and stirred for 8 h at room temperature. The reaction mixture was quenched with acetic acid and extracted with ethyl acetate. The combined ethyl acetate layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford 2.50 g (91.2%) of diethyl 2-(1-(pyridin-3-yl)propan-2-yl)malonate as pale brown oil.

Workup

  1. customThe reaction mixture was quenched with acetic acid
  2. extractionextracted with ethyl acetate
  3. washThe combined ethyl acetate layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b4a067cd7a2b4fe2ac6d78a0e71ebdb2
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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