Sodium hydride → HCID 18510245, compound

HRID 1371044Notes

Reaction equation

HRID 1371044 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)(=O)=O)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:24](Br)[CH:25]=[CH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C.C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:11]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)[CH2:24]/[CH:25]=[CH:26]/[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 98116BromomethylstyreneHCID 18510250HCID 18510250, compound

Product 1

HCID 18510245HCID 18510245, compoundYield 110.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 4-{[(4-fluorophenyl)sulfonyl]methyl}benzoate (0.26 g, 0.84 mmole) in DMF at 0° C. was added NaH (25 mg, 0.74 mmole) and the reaction was stirred for 15 minutes at 0° C. Then a solution of cinnamyl bromide (0.16 g, 0.81 mmole) in THF (1 mL) was added, and the reaction was allowed to warm to room temperature. The reaction was quenched with saturated NH4Cl solution and extracted with ethyl acetate. The organic phase was dried (Na2SO4), filtered, and evaporated. The residue was chromatographed to yield 0.35 g of the title compound.

Workup

  1. temperatureto warm to room temperature
  2. customThe reaction was quenched with saturated NH4Cl solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed

Sources & evidence

ORD record
ord-2a5dab4b452a4635ba231c1e3b97a400
Source dataset
uspto-grants-2003_06
Patent number
US06583126B2

Reaction notes

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