Ethyl cyanoacetate → (E)-ethyl 2-cyano-3-(4-phenoxyphenyl)acrylate

HRID 81040Notes

Reaction equation

HRID 81040 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10].[O:17]([C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[C:9](/[C:11](=[CH:28]\[C:27]1[CH:30]=[CH:31][C:24]([O:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:25][CH:26]=1)/[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 62657Potassium Phosphate, TribasicHCID 661394-Phenoxybenzaldehyde

Product 1

HCID 86665688(E)-ethyl 2-cyano-3-(4-phenoxyphenyl)acrylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Potassium phosphate (0.751 g, 3.54 mmol) was added to a solution of ethyl 2-cyanoacetate (2.00 g, 17.68 mmol) and 4-phenoxybenzaldehyde (3.50 g, 17.68 mmol) in ethanol (50 mL). After 1 h at room temperature, the mixture was quenched with water (20 mL). The ethanol solvent was evaporated in vacuo. The residue was taken up in ethyl acetate (150 mL), washed with brine (2×10 mL), dried (MgSO4) and concentrated. Silica gel chromatography, loading with toluene and eluting with 5 to 20% ethyl acetate in hexanes, gave (E)-ethyl 2-cyano-3-(4-phenoxyphenyl)acrylate as tan liquid. 1H NMR (500 MHz, CDCl3) δ ppm 8.19 (1H, s), 7.92-8.05 (2H, m), 7.37-7.48 (2H, m), 7.24 (1H, t, J=7.42 Hz), 7.10 (2H, δ, J=7.70 Hz), 6.98-7.07 (2H, m), 4.38 (2H, q, J=7.15 Hz), 1.40 (3H, δ, J=7.15 Hz); MS (ES+) m/z: 294 (M+H); LC retention time: 4.405 min (analytical HPLC Method B).

Workup

  1. customthe mixture was quenched with water (20 mL)
  2. customThe ethanol solvent was evaporated in vacuo
  3. washwashed with brine (2×10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washeluting with 5 to 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-437a03cf09474dd38450ff67c54fac39
Source dataset
uspto-grants-2014_09
Patent number
US08846673B2

Reaction notes

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