Water → 2-(2-Benzyloxyethyl)-2-phenylmalonic acid diethyl ester

HRID 494395Notes

Reaction equation

HRID 494395 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:19])[CH:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4].[CH2:20]([O:27][CH2:28][CH2:29]Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O>[CH2:11]([O:10][C:8](=[O:9])[C:7]([CH2:29][CH2:28][O:27][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:6]([O:5][CH2:3][CH3:4])=[O:19])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 66514Diethyl phenylmalonateHCID 73833Benzene, ((2-bromoethoxy)methyl)-

Product 1

HCID 576832242-(2-Benzyloxyethyl)-2-phenylmalonic acid diethyl esterYield 38.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (406 mg) was dissolved in dimethylformamide (20 mL) and the solution was cooled to 0° C. To this solution was added phenylmalonic acid diethyl ester (2.0 g), and the mixture was stirred at room temperature for 30 minutes. Bromoethyl benzyl ether (2.0 g) was further added thereto, stirred at 60° C. for 4 hours, and water was added thereto. The reaction mixture was concentrated, diluted with ethyl acetate, washed with water, dried over sodium sulfate and purified by column chromatography on silica gel with ethyl acetate:hexane=1:9 to give the title compound (1.2 g).

Workup

  1. stirringstirred at 60° C. for 4 hours
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. custompurified by column chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-171a3abf05d84595a30fdae97f9e96ce
Source dataset
uspto-grants-2009_05
Patent number
US07538140B2

Reaction notes

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