Ethyl cyanoacetate → 2-Phenylethyl cyanoacetate

HRID 1189598Notes

Reaction equation

HRID 1189598 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrC1C=CC=CC=1.C(P)=CC=C.[C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])#[N:21].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(#N)C>[C:20]([CH2:22][C:23]([O:25][CH2:26][CH2:27][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:24])#[N:21]

Participants

7

Reactant 5

HCID 7764Ethyl cyanoacetateHCID 7961BromobenzeneHCID 11575Iodobenzene2×HCID 62657Potassium Phosphate, TribasicHCID 54264816HCID 54264816, compound

Product 1

HCID 150272682-Phenylethyl cyanoacetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

The general procedure (acetonitrile, 82° C., 12 hours with iodobenzene; 30 hours in the case of bromobenzene) was followed using 9.52 mg (0.05 mmol) of copper iodide CuI, 31.4 mg (0.1 mmol) of (Z)-cinnamic butadienylphosphine of example A-1-1, 80 ml (0.75 mmol) of ethyl cyanoacetate, 318 mg (1.5 mmol) of potassium phosphate (K3PO4), 56 μl (0.5 mmol) of iodobenzene (53 μl of bromobenzene) and 500 μl of acetonitrile. The residue obtained after treatment (dichloromethane/water extraction) was purified by chromatography on a silica column (gradient: hexanes/CH2Cl2 100:0 to 75:25).

Workup

  1. custom30 hours
  2. customThe residue obtained
  3. extractionafter treatment (dichloromethane/water extraction)
  4. customwas purified by chromatography on a silica column (gradient: hexanes/CH2Cl2 100:0 to 75:25)

Sources & evidence

ORD record
ord-cca662e9e1044ab881a9b99a7c748f85
Source dataset
uspto-grants-2014_03
Patent number
US08674125B2

Reaction notes

Loading…