Methyl Acrylate → Dimethyl 4-(trifluoromethyl)-4-nitropimelate

HRID 37458

Reaction equation

HRID 37458 reaction equation
[F-].[K+].[C:3]([O:7][CH3:8])(=[O:6])[CH:4]=[CH2:5].[F:9][C:10]([F:16])([F:15])[CH2:11][N+:12]([O-:14])=[O:13]>C(#N)C>[F:9][C:10]([F:16])([F:15])[C:11]([N+:12]([O-:14])=[O:13])([CH2:5][CH2:4][C:3]([O:7][CH3:8])=[O:6])[CH2:5][CH2:4][C:3]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 522689Potassium FluorideHCID 5227621,1,1-Trifluoro-2-nitroethane

Product 1

HCID 14837690Dimethyl 4-(trifluoromethyl)-4-nitropimelate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

27 g (0.465 mol) of potassium fluoride (calcined) and 86 g (1 mol) of methyl acrylate are initially charged to 50 ml of acetonitrile at 0°-5° C. and 60 g (0.465 mol) of 2,2,2-trifluoronitroethane are added dropwise with stirring over a period of 60 min. The reaction is notably exothermic (up to about 60° C.). After being cooled to room temperature the reaction mixture is further stirred for 16 h. The mixture is filtered, the salt is washed with acetonitrile, and the solvent and unreacted starting material are stripped off on a rotary evaporator.

Workup

  1. customup to about 60° C.
  2. stirringis further stirred for 16 h
  3. filtrationThe mixture is filtered
  4. washthe salt is washed with acetonitrile
  5. customare stripped off on a rotary evaporator

Sources & evidence

ORD record
ord-1e2f3b3ce37a466987b15911964f1523
Source dataset
uspto-grants-1995_05
Patent number
US05420293

Linked notes

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