Sodium Chloride → HCID 58136329, compound

HRID 626411Notes

Reaction equation

HRID 626411 reaction equation
C(OP([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][C:21]=1[N+:28]([O-:30])=[O:29].[Cl-].[Na+]>C1COCC1>[F:19][C:20]1[CH:27]=[CH:26][C:23](/[CH:24]=[CH:9]/[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[CH:22][C:21]=1[N+:28]([O-:30])=[O:29]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 5981294-Fluoro-3-nitrobenzaldehydeHCID 2773685tert-Butyl diethylphosphonoacetate

Product 1

HCID 58136329HCID 58136329, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At RT and with slight cooling, 99.23 g (394 mmol) of tert-butyl diethylphosphonoacetate were added dropwise to a suspension of 15.74 g (394 mmol) of sodium hydride (60% in mineral oil) in 540 ml of THF. After the addition had ended, the mixture was stirred at RT for 30 min and, after cooling to 0° C., a solution of 60.5 g (358 mmol) of 4-fluoro-3-nitrobenzaldehyde in 324 ml of THF was added. The reaction mixture was stirred at RT overnight and then added to a 10% strength aqueous sodium chloride solution. The mixture was extracted twice with ethyl acetate. The combined organic phases were washed with sat. sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by chromatography (twice) on silica gel (mobile phase petroleum ether/ethyl acetate 9:1). This gave 82.0 g (84.9% of theory) of the target product.

Workup

  1. additionAfter the addition
  2. temperatureafter cooling to 0° C.
  3. stirringThe reaction mixture was stirred at RT overnight
  4. extractionThe mixture was extracted twice with ethyl acetate
  5. washThe combined organic phases were washed with sat. sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography (twice) on silica gel (mobile phase petroleum ether/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-42563a9087084b7f9e84e6f538b5cafd
Source dataset
uspto-grants-2016_04
Patent number
US09309198B2

Reaction notes

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