Triethyl phosphonoacetate → Ethyl 3-(4-fluorophenyl)prop-2-enoate

HRID 2086207Notes

Reaction equation

HRID 2086207 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:16])[CH2:7]P(OCC)(OCC)=O)[CH3:4].[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1>O1CCCC1>[CH2:3]([O:5][C:6](=[O:16])[CH:7]=[CH:22][C:21]1[CH:24]=[CH:25][C:18]([F:17])=[CH:19][CH:20]=1)[CH3:4]

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 367200Ethyl 3-(4-fluorophenyl)prop-2-enoateYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (2.11 g, 48.4 mmol) was suspended in anhydrous tetrahydrofuran (60 ml), and diethylphosphonoacetic acid ethyl ester (10.84 g, 48.4 mmol) was added dropwise thereto in an ice bath followed by stirring for 10 minutes. To this mixture solution, a solution of 4-fluorobenzaldehyde (5.00 g, 40.3 mmol) in anhydrous tetrahydrofuran (60 ml) was added dropwise at the same temperature. The reaction solution was stirred for 3 hours, and poured into ice-cold water (150 ml), and then extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was evaporated in vacuo, and then the residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=10:1-3:1) to give 4-fluorocinnamic acid ethyl ester (6.69 g, 86% yield) as a colorless oil.

Workup

  1. customin an ice bath followed
  2. stirringThe reaction solution was stirred for 3 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customthe residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=10:1-3:1)

Sources & evidence

ORD record
ord-ab8e80c0a9ad48ac8afc49eea1578720
Source dataset
uspto-grants-2004_04
Patent number
US06723745B2

Reaction notes

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