Diethyl Ether → HCID 72330510, compound

HRID 2098578Notes

Reaction equation

HRID 2098578 reaction equation
[Cr](Cl)([O-])(=O)=[O:2].[NH+]1C=CC=CC=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH2:37][OH:38])=[CH:20][C:21]2[CH:26]=[CH:25]C(C3C=C(C=CC=3)C(OC)=O)=[CH:23][CH:22]=2)=[CH:15][CH:14]=1.[CH2:39]([O:41][CH2:42][CH3:43])C>ClCCl>[F:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([CH:37]=[O:38])=[CH:20][C:21]2[CH:26]=[CH:25][C:43]([C:42]([O:41][CH3:39])=[O:2])=[CH:23][CH:22]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 68405934HCID 68405934, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 72330510HCID 72330510, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridinium chlorochromate (PCC) (1.12 g, 5.2 mmol) was dissolved in dichloromethane (20 mL). The solution of methyl 3-(4-(2-(4-fluorophenyl)-3-hydroxyprop-1-en-1-yl)phenyl)benzoate (1.14 g, 4 mmol) in dichloromethane (4 mL) was added dropwise under constant stirring and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with diethyl ether (100 mL) and filtered through celite; the filtrate was washed with saturated aqueous NaHCO3 solution (2×100 mL) and water (100 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to afford the pure title compound as a white solid (0.58 g, 53% yield)

Workup

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

Sources & evidence

ORD record
ord-d09161cdcf6f4cdbb5ab263cc5f3efcd
Source dataset
uspto-grants-2013_05
Patent number
US08450525B2

Reaction notes

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