Sodium hydride → HCID 12363573, compound

HRID 2114175Notes

Reaction equation

HRID 2114175 reaction equation
[H-].[Na+].[C:3]1([CH:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:18]([O:17][C:15](=[O:16])[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:19]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 66514Diethyl phenylmalonateHCID 68320Ethyl 3-bromopropionate

Product 1

HCID 12363573HCID 12363573, compoundYield 109.7%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (520 mg) was dissolved in THF (7 ml), and the solution was cooled to 0° C. and thereto were added diethyl 2-phenylmalonate (2.36 g) and tetrabutyl ammonium iodide (6 mg). The resulting mixture was stirred at room temperature for 0.5 hour and ethyl 3-bromopropionate (1.3 g) was added. The mixture was stirred at room temperature for 4 hours. The reaction solution was filtered through a Celite, and the filtrate was concentrated and purified by column chromatography on silica gel (ethyl acetate:hexane=1:7) to give 2-ethoxycarbonyl-2-phenylpentanedioic acid diethyl ester (2.65 g).

Workup

  1. stirringThe mixture was stirred at room temperature for 4 hours
  2. filtrationThe reaction solution was filtered through a Celite
  3. concentrationthe filtrate was concentrated
  4. custompurified by column chromatography on silica gel (ethyl acetate:hexane=1:7)

Sources & evidence

ORD record
ord-aa10541b4a6145149e268fd9b108a895
Source dataset
uspto-grants-2008_10
Patent number
US07432392B2

Reaction notes

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