Water → Ethyl 3-(3-furanyl)-3-oxo-2-((4-(trifluoromethyl)phenyl)methyl)propionate

HRID 1610420Notes

Reaction equation

HRID 1610420 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6](=[O:13])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:2]1.[H-].[Na+].[F:16][C:17]([F:27])([F:26])[C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1.O>COCCOC>[O:1]1[CH:5]=[CH:4][C:3]([C:6](=[O:13])[CH:7]([CH2:22][C:21]2[CH:20]=[CH:19][C:18]([C:17]([F:16])([F:26])[F:27])=[CH:25][CH:24]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 336409Ethyl 3-(furan-3-yl)-3-oxopropanoate

Product 1

HCID 22262074Ethyl 3-(3-furanyl)-3-oxo-2-((4-(trifluoromethyl)phenyl)methyl)propionateYield 77%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of ethyl 3-(3-furanyl)-3-oxopropionate (20 g, 110 mmol) in 1,2-dimethoxyethane (100 ml) was added sodium hydride (60% in oil, 4.4 g, 110 mmol) under ice-cooling and the mixture was stirred at room temperature for 30 min. To the reaction solution was dropwise added a solution of 4-trifluoromethylbenzyl bromide (26.2 g, 110 mmol) in 1,2-dimethoxyethane (50 ml) and the reaction solution was stirred at room temperature for 3 hrs. The reaction solution was poured into water (300 ml) and extracted with ethyl acetate (500 ml×2). The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from diisopropyl ether-hexane to give ethyl 3-(3-furanyl)-3-oxo-2-((4-(trifluoromethyl)phenyl)methyl)propionate (28.8 g, 77%).

Workup

  1. temperaturecooling
  2. stirringthe reaction solution was stirred at room temperature for 3 hrs
  3. extractionextracted with ethyl acetate (500 ml×2)
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was recrystallized from diisopropyl ether-hexane

Sources & evidence

ORD record
ord-bdefa72b428242fe9477ef538138ca19
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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