Sodium hydride → HCID 53948311, compound

HRID 993047Notes

Reaction equation

HRID 993047 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[H-].[Na+].[C:20]1([CH3:31])[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH2:29]Br)=[CH:22][CH:21]=1>O1CCCC1>[CH2:9]([O:8][C:6](=[O:7])[C:5]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH2:29][CH2:28][CH2:27][CH2:26][C:23]1[CH:22]=[CH:21][C:20]([CH3:31])=[CH:25][CH:24]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:17])[CH3:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66514Diethyl phenylmalonateHCID 18408742HCID 18408742, compound

Product 1

HCID 53948311HCID 53948311, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Phenylmalonic acid diethyl ester (8.8 mmol) dissolved in 5 ml absolute tetrahydrofuran is added dropwise to 20 ml absolute tetrahydrofuran and sodium hydride (9.7 mmol). Then 4-p-tolylbutyl bromide (8.8 mmol) dissolved in 10 ml absolute tetrahydrofuran is added after 15 minutes. It is heated for 3 days under reflux. The solvent is concentrated in a vacuum. The residue is taken up in 50 ml ethyl acetate and extracted with 2×50 ml water. The organic phase is dried over magnesium sulfate, filtered and concentrated by evaporation. It is purified by chromatography on silica gel (heptane/ethyl acetate 9:1). Yield 55% colourless oil.

Workup

  1. additionis added after 15 minutes
  2. temperatureIt is heated for 3 days
  3. temperatureunder reflux
  4. concentrationThe solvent is concentrated in a vacuum
  5. extractionextracted with 2×50 ml water
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. customIt is purified by chromatography on silica gel (heptane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-734850e9383848738f23e0464fb11f1b
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

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