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Sodium hydride → Ethyl 3-(3-chlorophenyl)-3-oxo-2-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]propionate

HRID 1610753
Notes
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Reaction equation

HRID 1610753 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([F:33])([F:32])[C:28]([F:31])([F:30])[F:29])=[CH:22][CH:21]=1>C(COC)OC>[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[O:15])[CH:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]([F:32])([F:33])[C:28]([F:29])([F:30])[F:31])=[CH:22][CH:21]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2757831Ethyl 3-(3-chlorophenyl)-3-oxopropanoateHCID 222623121-(Bromomethyl)-4-(2,2,3,3,3-pentafluoropropyl)benzene

Product 1

HCID 22262239Ethyl 3-(3-chlorophenyl)-3-oxo-2-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]propionateYield 86%

Reagents, catalysts & solvents 1

HCID 8071
1,2-Dimethoxyethane
Solvent
2×

Procedure

A solution of ethyl 3-(3-chlorophenyl)-3-oxopropionate (2.74 g, 12.08 mmol) in dimethoxyethane (30 ml) was ice-cooled, and sodium hydride (60%, 0.49 g, 12.08 mmol) was added, and the mixture was stirred under ice-cooling for 30 min. A solution of 1-(bromomethyl)-4-(2,2,3,3,3-pentafluoropropyl)benzene (3.66 g, 12.08 mmol) in dimethoxyethane (15 ml) was added, and the mixture was stirred overnight at room temperature. After completion of the reaction, the reaction was quenched with 0.5N hydrochloric acid. The mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1, 10:1) to give ethyl 3-(3-chlorophenyl)-3-oxo-2-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]propionate (4.64 g, 86%) as colorless crystals.

Workup

  1. temperaturecooled
  2. temperaturecooling for 30 min
  3. stirringthe mixture was stirred overnight at room temperature
  4. customAfter completion of the reaction
  5. customthe reaction was quenched with 0.5N hydrochloric acid
  6. additionThe mixture was diluted with ethyl acetate
  7. washwashed with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1, 10:1)

Sources & evidence

ORD record
ord-12ea1a19cc464a46b07b887b603f6c5a
Source dataset
uspto-grants-2006_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06982348B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes