Dimethylcarbamoyl Chloride → tert-Butyl (E)-3-(6-cyano-2-pyridyl)-2-propenoate

HRID 499402Notes

Reaction equation

HRID 499402 reaction equation
[O-][N+:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C[Si]([C:21]#[N:22])(C)C.CN(C)C(Cl)=O.C(OCC)(=O)C>[N+](CC)([O-])=O.O>[C:21]([C:7]1[N:2]=[C:3](/[CH:8]=[CH:9]/[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:4]=[CH:5][CH:6]=1)#[N:22]

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8857Ethyl AcetateHCID 82115Trimethylsilyl cyanideHCID 597502862-(3-Oxo-3-tert-butoxy-1-propenyl)pyridine 1-oxide

Product 1

HCID 70859748tert-Butyl (E)-3-(6-cyano-2-pyridyl)-2-propenoateYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6587NitroethaneSolvent

Procedure

tert-Butyl (E)-3-(1-oxido-2-pyridyl)-2-propenoate (2.10 g, 9.5 mmol) was dissolved in nitroethane (10 ml), and trimethylsilyl cyanide (1.88 g, 19.0 mmol) and N,N-dimethylcarbamoyl chloride (2.04 g, 19.0 mmol) were added thereto. The reaction mixture was stirred at room temperature for 18 hrs and combined with ethyl acetate and water. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate. The solvent was evaporated. The residue was subjected to a silica gel column chromatography. The fractions eluted with hexane-ethyl acetate (5:1, v/v) were collected and concentrated to give the titled compound (2.18 g, ca. 100%).

Workup

  1. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. washThe fractions eluted with hexane-ethyl acetate (5:1
  5. customv/v) were collected
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-715a91175d274689b7936e17bd7976d4
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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