Water → tert-Butyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate

HRID 1476055Notes

Reaction equation

HRID 1476055 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[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>[Cl: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 855054-Chloro-3-nitrobenzaldehydeHCID 2773685tert-Butyl diethylphosphonoacetate

Product 1

HCID 58136394tert-Butyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under argon, 1.19 g (29.64 mmol, 60%) of sodium hydride were suspended in 25 ml of toluene and 25 ml of THF, and the mixture was cooled to 0° C. 7.28 ml (30.99 mmol) of tert-butyl (diethoxyphosphoryl)acetate were then slowly added dropwise, and the mixture was stirred at 0° C. for 30 min. 5 g (26.94 mmol) of 4-chloro-3-nitrobenzaldehyde were then added to the reaction mixture, and the mixture was subsequently warmed to room temperature. The mixture was stirred at room temperature for 2 h, and 50 ml of water were then added. The organic phase was separated off, and the aqueous phase was then extracted three more times with ethyl acetate. The combined organic phases were dried over sodium sulphate. After filtration, the solvent was removed under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 9:1). This gave 6.77 g (23.86 mmol, 77% of theory) of the title compound.

Workup

  1. temperaturethe mixture was subsequently warmed to room temperature
  2. stirringThe mixture was stirred at room temperature for 2 h
  3. customThe organic phase was separated off
  4. extractionthe aqueous phase was then extracted three more times with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulphate
  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 9:1)

Sources & evidence

ORD record
ord-76f94c2651d04692abe1d313affe4b41
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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