Ethyl cyanoacetate → HCID 118863127, compound

HRID 63923Notes

Reaction equation

HRID 63923 reaction equation
Br[CH:2]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)=[O:4].[C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])#[N:21].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CC(=O)OCC.O>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][CH:2]([C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=2)=[O:4])[CH:22]([C:20]#[N:21])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:14][CH:15]=1

Participants

7

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 11430Potassium CarbonateHCID 1188630992-Bromo-1-(3-chlorophenyl)-3-(4-chlorophenyl)propan-1-one

Product 1

HCID 118863127HCID 118863127, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-1-(3-chlorophenyl)-3-(4-chlorophenyl)propan-1-one (358 mg, 1 mmol) in DMF (3 mL) was added ethyl 2-cyanoacetate (226 mg, 2 mmol), followed by K2CO3 (276 mg, 2 mmol). The reaction was stirred at RT for 2 h then diluted with EA (10 mL) and water (3 mL). The organic layer was washed with brine (3 mL), dried over Na2SO4 and concentrated to give ethyl 3-(4-chlorobenzyl)-4-(3-chlorophenyl)-2-cyano-4-oxobutanoate (300 mg, 77% yield) as a yellow solid. LCMS: MH+ 390 and TR=2.334 min. Used without further purification.

Workup

  1. washThe organic layer was washed with brine (3 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6a72a46df0214eceaeba892a243c550a
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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