Dimethylformamide → HCID 67382967, compound

HRID 2176900Notes

Reaction equation

HRID 2176900 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-f77ee7280a7f422c8b9875f3137ecb27
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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