Sodium hydride → Methyl 3-[(e)-1-(4-fluorobenzoyl)-4-phenyl-3-butenyl]benzoate

HRID 1371030Notes

Reaction equation

HRID 1371030 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH2:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])=[CH:4][CH:3]=1.[CH2:21](Br)[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[H-].[Na+].[NH4+].[Cl-]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH:9]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH2:21]/[CH:22]=[CH:23]/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:20])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 98116BromomethylstyreneHCID 18510261Methyl 3-[2-(4-fluorophenyl)-2-oxoethyl]benzoate

Product 1

HCID 18510225Methyl 3-[(e)-1-(4-fluorobenzoyl)-4-phenyl-3-butenyl]benzoateYield 87.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product from Step 1 (1.0 g, 3.7 mmol) and cinnamyl bromide (0.72 g, 3.7 mmol) in DMF (15 mL) at 0° C. under N2 was added the NaH (121 mg, 4.0 mmol, 80% in oil). After 20 min. at 0° C., the reaction was stirred for 1 h at r.t. Saturated NH4Cl (15 mL) was then added and the product was extracted with Et2O. The organic phase was washed with H2O and brine, and was then dried (MgSO4) filtered, and evaporated. The residue was purified by flash chromatography (1:10 EtOAc:hexane) to give a colourless oil (1.26 g).

Workup

  1. extractionthe product was extracted with Et2O
  2. washThe organic phase was washed with H2O and brine
  3. dry with materialwas then dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography (1:10 EtOAc:hexane)

Sources & evidence

ORD record
ord-1f8e870885524a499154f697da8702ca
Source dataset
uspto-grants-2003_06
Patent number
US06583126B2

Reaction notes

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