2-Benzyl-malonic acid monoethyl ester → HCID 13138320, compound

HRID 905361Notes

Reaction equation

HRID 905361 reaction equation
[CH2:1]([O:3][P:4]([O-:8])[O:5][CH2:6][CH3:7])[CH3:2].[CH2:9]([O:11][C:12](=[O:22])[C:13]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH2:14])[CH3:10].C(OC(=O)C(CC1C=CC=CC=1)C(O)=O)C.[Na]>C(O)C>[CH2:9]([O:11][C:12](=[O:22])[CH:13]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:14][P:4]([O:5][CH2:6][CH3:7])([O:3][CH2:1][CH3:2])=[O:8])[CH3:10]

Participants

6

Reactant 4

HCID 28848672-Benzyl-malonic acid monoethyl esterHCID 3780918DiethylphosphiteHCID 5360545SodiumHCID 11084648Ethyl 2-benzylacrylate

Product 1

HCID 13138320HCID 13138320, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of diethylphosphite (6.9 g) and 2-benzylacrylic acid ethyl ester (9.5 g) (prepared according to the procedure of C. Mannich and K. Risert Ber. (1924), 57, 1116 from benzylmalonic acid mono ethyl ester) was added, with stirring at ambient temperature under an atmosphere of nitrogen, a solution of sodium (1.15 g) in ethanol (20 ml). Following the initial exothermic reaction stirring was continued for 48 hr. The solvent was evaporated in vacuo and the residual gum partitioned between ether (100 ml) and 5% CA (50 ml). The ether solution was shaken once more with 5% CA (50 ml), dried (MgSO4) and the residue distilled, collecting the fraction (3.7 g) m.p. 58°-72°/0.02-0.03 mm). The structure of the product was confirmed by NMR and Mass spectroscopy.

Workup

  1. customprepared
  2. customexothermic reaction
  3. stirringstirring
  4. customThe solvent was evaporated in vacuo
  5. customthe residual gum partitioned between ether (100 ml) and 5% CA (50 ml)
  6. stirringThe ether solution was shaken once more with 5% CA (50 ml)
  7. dry with materialdried (MgSO4)
  8. distillationthe residue distilled
  9. customcollecting the fraction (3.7 g) m.p. 58°-72°/0.02-0.03 mm)

Sources & evidence

ORD record
ord-44fdda26500243ed89f7f1096bcc2ff0
Source dataset
uspto-grants-1983_12
Patent number
US04423242

Reaction notes

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