Ethyl Acetate → HCID 23233793, compound

HRID 859219Notes

Reaction equation

HRID 859219 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:20]=[CH:19][C:9]([CH2:10]P(=O)(OCC)OCC)=[CH:8][CH:7]=1)([O-:5])=[O:4].[F:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O.C(OCC)(=O)C>CN(C)C=O>[F:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:24](/[CH:25]=[CH:10]/[C:9]2[CH:8]=[CH:7][C:6]([N+:3]([O-:5])=[O:4])=[CH:20][CH:19]=2)[CH:23]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 680093-FluorobenzaldehydeHCID 256065Diethyl 4-nitrobenzylphosphonate

Product 1

HCID 23233793HCID 23233793, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 677 mg of sodium hydride (55% dispersion in oil) in 10 ml of N,N-dimethylformamide is cooled to 0° C. Thereupon, 5.61 g (20.5 mmol) of diethyl (4-nitrobenzyl)phosphonate are added portionwise. The reaction mixture is left to warm to RT and stirred for 1.5 hours. Thereafter, the mixture is cooled to −10° C. and a solution of 1.5 g (12.1 mmol) of 3-fluorobenzaldehyde in 5 ml N,N-dimethylformamide is added dropwise. Stirring is continued for 30 min at 0° C., then at RT. For the working-up, ice and ethyl acetate are added to the reaction mixture. The organic layer is separated, dried over magnesium sulfate and evaporated under reduced pressure to yield the crude crystalline product, which after recrystallisation from a mixture of ether and heptane gives 2.41 g (82% of theory) of (E)-1-fluoro-3-[2-(4-nitrophenyl)ethenyl]-benzene as a yellow solid; MS: m/e=243(M)+.

Workup

  1. waitThe reaction mixture is left
  2. temperatureto warm to RT
  3. temperatureThereafter, the mixture is cooled to −10° C.
  4. stirringStirring
  5. waitis continued for 30 min at 0° C.
  6. customat RT
  7. customThe organic layer is separated
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under reduced pressure
  10. customto yield the crude crystalline product, which
  11. customafter recrystallisation
  12. additionfrom a mixture of ether and heptane

Sources & evidence

ORD record
ord-22618b49f2804870a7698040acb34723
Source dataset
uspto-grants-2006_12
Patent number
US07151111B2

Reaction notes

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