Water → HCID 58136329, compound

HRID 877209Notes

Reaction equation

HRID 877209 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(OCC)=O)C.[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].O>C1(C)C=CC=CC=1.C1COCC1>[F:19][C:20]1[CH:27]=[CH:26][C:23](/[CH:24]=[CH:11]/[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[CH:22][C:21]=1[N+:28]([O-:30])=[O:29]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5981294-Fluoro-3-nitrobenzaldehydeHCID 2773685tert-Butyl diethylphosphonoacetate

Product 1

HCID 58136329HCID 58136329, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under argon, 130.1 mg (3.25 mmol) of sodium hydride were initially charged in 2 ml of toluene and 2 ml of THF. The mixture was cooled to 0° C., and 857.7 mg (3.40 mmol) of tert-butyl (diethoxyphosphoryl)acetate were added slowly. The mixture was stirred for another 30 min, and 500 mg (2.96 mmol) of 4-fluoro-3-nitrobenzaldehyde were then added. The reaction mixture was slowly warmed to RT and stirred for 3 h. The reaction mixture was then added to water and extracted three times with ethyl acetate. The organic phase was concentrated under reduced pressure and the residue purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 30:1→10:1). This gave 543 mg (69% of theory) of the title compound.

Workup

  1. temperatureThe reaction mixture was slowly warmed to RT
  2. stirringstirred for 3 h
  3. extractionextracted three times with ethyl acetate
  4. concentrationThe organic phase was concentrated under reduced pressure
  5. customthe residue purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 30:1→10:1)

Sources & evidence

ORD record
ord-09fe26c1689345ae844615182763359f
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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