Triethyl phosphonoacetate → HCID 86758305, compound

HRID 2227502Notes

Reaction equation

HRID 2227502 reaction equation
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH3:17][O:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=O)[CH3:28])=[CH:23][CH:22]=1>O1CCCC1>[CH3:17][O:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24](/[C:27](/[CH3:28])=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:23][CH:22]=1.[CH3:17][O:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24](/[C:27](/[CH3:28])=[CH:9]\[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 44249974'-(METHOXYMETHOXY)ACETOPHENONE

Product 2

HCID 86758305HCID 86758305, compoundYield 42%HCID 86758306HCID 86758306, compoundYield 4.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

9 ml of ethyl diethylphosphonoacetate was added dropwise to a suspension of 60% sodium hydride in oil (1.93 g) in 40 ml tetrahydrofuran and stirred at room temperature for 30 minutes. A solution of 4′-(methoxymethoxy)acetophenone (6.70 g) in 40 ml tetrahydrofuran was added dropwise to the reaction mixture, followed by stirring at room temperature for 17 hours and subsequently at reflux for 4 days. The solvent was evaporated, and the reaction mixture was mixed with water and then extracted with ethyl acetate. The resulting organic layer was washed with water and brine, and then dried over magnesium sulfate. The drying agent was filtered off and the solvent was evaporated to give a residue, which was then purified via column chromatography on silica gel (hexane:ethyl acetate=10:1) to provide ethyl (E)-3-[4-(methoxymethoxy)phenyl]-2-butenoate (3.91 g, 42%) as a colorless oil and ethyl (Z)-3-[4-(methoxymethoxy)phenyl]-2-butenoate (425 mg, 4.6%) as a colorless oil, respectively.

Workup

  1. stirringby stirring at room temperature for 17 hours
  2. temperaturesubsequently at reflux for 4 days
  3. customThe solvent was evaporated
  4. additionthe reaction mixture was mixed with water
  5. extractionextracted with ethyl acetate
  6. washThe resulting organic layer was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationThe drying agent was filtered off
  9. customthe solvent was evaporated
  10. customto give a residue, which
  11. customwas then purified via column chromatography on silica gel (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-f800f1e0804647d88567fd9d8e3bbba0
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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