HCID 68415655, compound → HCID 86761864, compound

HRID 2098568Notes

Reaction equation

HRID 2098568 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH2:33][OH:34])=[CH:20][C:21]2[CH:26]=[CH:25][C:24](/[CH:27]=[CH:28]/[C:29]([O:31][CH3:32])=[O:30])=[CH:23][CH:22]=2)=[CH:15][CH:14]=1>ClCCl.C(OCC)C>[F:12][C:13]1[CH:18]=[CH:17][C:16](/[C:19](/[CH:33]=[O:34])=[CH:20]\[C:21]2[CH:26]=[CH:25][C:24]([CH:27]=[CH:28][C:29]([O:31][CH3:32])=[O:30])=[CH:23][CH:22]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 68415655HCID 68415655, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86761864HCID 86761864, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of pyridinium chlorochromate (PCC, 0.75 g, 3.5 mmol) in dichloromethane (20 mL) a dropwise solution of methyl 3-(E)(4-(2-(4-fluorophenyl)-3-hydroxyprop-1-en-1-yl)phenyl)acrylate (0.9 g, 2.9 mmol) in dichloromethane (5 mL) was added under constant stirring and the reaction mixture was stirred at room temperature for 1 hour. The reaction mass was diluted with diethyl ether (200 mL) and filtered through a celite bed, the filtrate was successively washed with saturated aqueous NaHCO3 solution (3×100 mL) and water (1×100 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to afford the pure title compound as a white solid (0.5 g, 56% yield).

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred at room temperature for 1 hour
  3. filtrationfiltered through a celite bed
  4. washthe filtrate was successively washed with saturated aqueous NaHCO3 solution (3×100 mL) and water (1×100 mL)
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3d9089159a514144875d996e00029f8c
Source dataset
uspto-grants-2013_05
Patent number
US08450525B2

Reaction notes

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