Water → HCID 58136333, compound

HRID 877216Notes

Reaction equation

HRID 877216 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.[Cl:19][C:20]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O.O>C1(C)C=CC=CC=1.C1COCC1>[Cl:19][C:20]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=[CH:24][C:21]=1/[CH:22]=[CH:11]/[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2773685tert-Butyl diethylphosphonoacetateHCID 126677132-Chloro-3-nitrobenzaldehyde

Product 1

HCID 58136333HCID 58136333, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under argon, 98 mg (2.46 mmol, 60% pure) of sodium hydride were suspended in 2 ml of toluene and 2 ml of THF, and the suspension was cooled to 0° C. 0.6 ml (2.57 mmol) of tert-butyl (diethoxyphosphoryl)acetate was then slowly added dropwise, and the mixture was stirred at 0° C. for 30 min. 415 mg (2.24 mmol) of 2-chloro-3-nitrobenzaldehyde were then added to the reaction mixture, and the reaction mixture was then warmed to room temperature. The mixture was stirred at room temperature for 2 hours, and 5 ml of water were then added. After removal of the organic phase, the aqueous phase was extracted three more times with ethyl acetate. The combined organic phases were dried over sodium sulfate. After filtration, the solvent was removed under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 10:1). This gave 429 mg (1.51 mmol, 59% of theory) of the title compound.

Workup

  1. temperaturethe reaction mixture was then warmed to room temperature
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. customAfter removal of the organic phase
  4. extractionthe aqueous phase was extracted three more times with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was removed under reduced pressure
  8. customThe crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-a4621d9596054b2496092b9bb8a5701c
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

Loading…