Water → Ethyl 3-(4-fluorophenyl)-2-(4-isopropylbenzyl)-3-oxopropionate

HRID 1610298Notes

Reaction equation

HRID 1610298 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH:18]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1)([CH3:20])[CH3:19].O>COCCOC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](=[O:7])[CH:8]([CH2:25][C:24]2[CH:27]=[CH:28][C:21]([CH:18]([CH3:20])[CH3:19])=[CH:22][CH:23]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 749164-Isopropylbenzyl chlorideHCID 2758844Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate

Product 1

HCID 22261387Ethyl 3-(4-fluorophenyl)-2-(4-isopropylbenzyl)-3-oxopropionate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of ethyl (4-fluorobenzoyl)acetate (23.21 g, 110.4 mmol) in 1,2-dimethoxyethane (150 ml) was added a suspension (4.42 g, 110 mmol) of 60% sodium hydride in liquid paraffin under ice-cooling and the mixture was stirred as it was for 0.5 hr. A solution of 4-isopropylbenzyl chloride (18.6 g 110 mmol) in 1,2-dimethoxyethane (50 ml) was added at room temperature and the mixture was stirred at 70° C. overnight. The reaction solution was poured into water and extracted twice with ethyl acetate. The collected organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1-9/1) to give the objective substance.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 70° C. overnight
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe collected organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1-9/1)
  7. customto give the objective substance

Sources & evidence

ORD record
ord-083e639bff5845638696289cb4bbee0c
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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