Triethyl phosphonoacetate → HCID 14417393, compound

HRID 519073Notes

Reaction equation

HRID 519073 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].C(N(C(C)C)C(C)C)C.[Cl-].[Li+].C(OP([CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])(OCC)=O)C>CC#N>[N+:1]([C:4]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:5]=1/[CH:6]=[CH:34]/[C:35]([O:37][CH2:38][CH3:39])=[O:36])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 13345Triethyl phosphonoacetateHCID 682502,4-DinitrobenzaldehydeHCID 81531DiisopropylethylamineHCID 433294Lithium Chloride

Product 1

HCID 14417393HCID 14417393, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 2,4-dinitrobenzaldehyde (12.0 g, 61.2 mmol), N-ethyl-N-isopropylpropan-2-amine (11.9 g, 91.8 mmol) and lithium chloride (3.1 g, 24.1 mmol) in CH3CN (100 mL) was added slowly ethyl 2-(diethoxyphosphoryl)acetate (16.5 g, 64.3 mmol) and the reaction mixture was stirred at ambient temperature for 12 h. After filtration, the solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (eluting with 4% EtOAc in petroleum ether) to give (E)-ethyl 3-(2,4-dinitrophenyl)acrylate (13 g, 84%). 1H NMR (CDCl3, 400 MHz): δ 8.83 (s, 1H), 8.42 (d, J=8.8 Hz, 1H), 8.02 (d, J=16.0 Hz, 1H), 7.77 (d, J=8.8 Hz, 1H), 6.39 (d, J=16.0 Hz, 1H), 4.24 (q, J=7.2 Hz, 2H), 1.29 (t, J=7.2 Hz, 3H).

Workup

  1. filtrationAfter filtration
  2. customthe solvent was removed in vacuo
  3. customthe residue was purified by column chromatography on silica gel (eluting with 4% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-d57440559aa24f1e85666c07464c1868
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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