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Sodium hydride → methyl 4-[(E)-1-(4-fluorobenzoyl)-4-phenyl-3-butenyl]benzoate

HRID 1371049
Notes
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Reaction equation

HRID 1371049 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[O:12])=[CH:6][CH:5]=1.[H-].[Na+].[CH2:23](Br)[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[F:19][C:16]1[CH:15]=[CH:14][C:13]([C:11]([CH:10]([C:7]2[CH:6]=[CH:5][C:4]([C:3]([O:2][CH3:1])=[O:20])=[CH:9][CH:8]=2)[CH2:23]/[CH:24]=[CH:25]/[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:12])=[CH:18][CH:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 98116BromomethylstyreneHCID 18510220Methyl 4-[2-(4-fluorophenyl)-2-oxoethyl]benzoate

Product 1

HCID 18510204methyl 4-[(E)-1-(4-fluorobenzoyl)-4-phenyl-3-butenyl]benzoateYield 72.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 4-[2-((4-fluorophenyl)-2-oxoethyl]benzoate (Example 1, Step 2) (1.0 g, 3.67 mmole) in DMF (10 mL) at 0° C. was added NaH (0.105 mg, 3.6 mmol). After stirring for 10 minutes at 0° C., cinnamyl bromide (0.71 g, 3.6 mmole) was added to the mixture. The reaction was stirred for r.t. for 1 h. and was then quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic phase dried (Na2SO4), filtered, and evaporated. The residue was purified by flash chromatography to yield 1.02 g of the desired product.

Workup

  1. stirringThe reaction was stirred for r.t. for 1 h.
  2. customwas then quenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-8c4d165366464f9792c0369fe085d445
Source dataset
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06583126B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes