Water → 2-(2-Benzyloxyethyl)malonic acid tert-butyl ester ethyl ester

HRID 1459881Notes

Reaction equation

HRID 1459881 reaction equation
[H-].[Na+].[C:3]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH2:17][CH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[CH2:8]([O:7][C:5](=[O:6])[CH:4]([CH2:17][CH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:3]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH3:9]

Participants

8

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 96345tert-Butyl ethyl malonate

Product 1

HCID 538022602-(2-Benzyloxyethyl)malonic acid tert-butyl ester ethyl esterYield 80%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride (3.22 g, 0.134 mole) in N,N-dimethylformamide (DMF)(150 mL) was added tert-butyl ethyl malonate (22.9 g, 0.122 mole). The resulting mixture was stirred at room temperature for 1 hour and then a solution of (2-bromoethoxymethyl)benzene (28.8 g, 0.134 mole) in DMF (150 mL) was added dropwise. After stirring at room temperature overnight, the mixture was poured into water (1000 mL) and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, dried over magnesium sulfate and concentrated to an oil which was chromatographed on silica gel eluting with hexane and then 5% ethyl acetate in hexane to afford 2-(2-benzyloxyethyl)malonic acid tert-butyl ester ethyl ester as an oil (31.4 g, 80% yield).

Workup

  1. stirringAfter stirring at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to an oil which
  6. customwas chromatographed on silica gel eluting with hexane

Sources & evidence

ORD record
ord-16344f8a444c432c879533d6d58a6199
Source dataset
uspto-grants-1998_12
Patent number
US05854275

Reaction notes

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