Sodium hydride → Methyl 3-[4-(2-chloroethoxy)phenyl]-2-ethoxy-2-propenoate

HRID 1790238Notes

Reaction equation

HRID 1790238 reaction equation
[H-].[Na+].[CH2:3]([O:5][CH:6](P(OCC)(OCC)=O)[C:7]([O:9][CH3:10])=[O:8])[CH3:4].[Cl:19][CH2:20][CH2:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1>O1CCCC1>[Cl:19][CH2:20][CH2:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[C:6]([O:5][CH2:3][CH3:4])[C:7]([O:9][CH3:10])=[O:8])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1431564-(2-Chloroethoxy)benzaldehydeHCID 86760126Methyl 2-ethoxy-2-diethylphosphonoacetate

Product 1

HCID 69597529Methyl 3-[4-(2-chloroethoxy)phenyl]-2-ethoxy-2-propenoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 150 ml of freshly distilled tetrahydrofuran, placed in a bath of ice-cold water at 0° C., under argon, add sodium hydride (0.0473 mol) and then methyl 2-ethoxy-2-diethylphosphonoacetate (0.0394 mol) while maintaining the temperature at 0° C. After stirring for 1 hour, add 4-(2-chloroethoxy)benzaldehyde (0.0394 mol) dissolved in a minimum of freshly distilled tetrahydrofuran, under argon at 0° C. Stir the solution for 1 hour at 0° C. Allow the solution to return to ambient temperature while stirring for 16 hours. Evaporate off the tetrahydrofuran. Add 100 ml of water and then extract with 100 ml of dichloromethane twice. The organic phase is washed with water, dried over MgSO4 and then evaporated. The oily product is purified over a column of silica gel using the eluant mixture: petroleum ether/dichloromethane (1/1). The title compound is obtained in the form of an oil.

Workup

  1. stirringStir the solution for 1 hour at 0° C
  2. customto return to ambient temperature
  3. stirringwhile stirring for 16 hours
  4. customEvaporate off the tetrahydrofuran
  5. additionAdd 100 ml of water
  6. extractionextract with 100 ml of dichloromethane twice
  7. washThe organic phase is washed with water
  8. dry with materialdried over MgSO4
  9. customevaporated
  10. customThe oily product is purified over a column of silica gel using the eluant mixture

Sources & evidence

ORD record
ord-556fc30c333c40f3bdcee69717499612
Source dataset
uspto-grants-2006_07
Patent number
US07071221B2

Reaction notes

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