Toluene → HCID 59443045, compound

HRID 1959115Notes

Reaction equation

HRID 1959115 reaction equation
[I-].[NH4+].S([O-])([O-])(=O)=O.[Ca+2].C([N:11](CC)CC)C.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=O)=[C:19]([OH:32])[CH:18]=1.[C:33]1(C)[CH:38]=[CH:37]C=[CH:35][CH:34]=1>C(#N)C.CCC(=O)CC>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]2[C:23]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[N:11][C:33]([CH2:38][CH3:37])([CH2:34][CH3:35])[O:32][C:19]=2[CH:18]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 8471TriethylamineHCID 24497Calcium SulfateHCID 25487Ammonium iodideHCID 10060688HCID 10060688, compound

Product 1

HCID 59443045HCID 59443045, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 7288Ethyl ketoneSolvent

Procedure

Ammonium iodide (724 mg), calcium sulfate (trade name: Drierite, 626 mg) and triethylamine (697 μL) were added to a solution of (4-chloro-2-hydroxyphenyl)(4-fluorophenyl)methanone (251 mg) in acetonitrile (3 mL) and the mixture was stirred under argon atmosphere at room temperature for 2 hours. A solution of 3-pentanone (318 μL) in acetonitrile (1 mL) was added to the reaction mixture. The mixture was stirred at 85° C. overnight and further heated under reflux overnight after the addition of toluene (10 mL). The reaction solution was filtered and the filtrate was concentrated in vacuo. A solution of the resultant residue in isopropyl ether was washed successively with an aqueous 0.1N sodium hydroxide solution, water and brine, filtered through a column of porous diatomite (Chem Elut) and a column of solid phase extraction (Bond Elut jr NH2 (trade name); Varian Inc.). The filtrate was concentrated in vacuo and the resultant residue was purified by column chromatography on NH-silica gel (Chromatorex NH silica gel, Solvent: n-hexane/ethyl acetate=100/0 to 95/5) to give the titled compound (113 mg) as a yellow oil.

Workup

  1. stirringThe mixture was stirred at 85° C. overnight
  2. temperaturefurther heated
  3. temperatureunder reflux overnight
  4. filtrationThe reaction solution was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. washA solution of the resultant residue in isopropyl ether was washed successively with an aqueous 0.1N sodium hydroxide solution, water and brine
  7. filtrationfiltered through a column of porous diatomite (Chem Elut)
  8. extractiona column of solid phase extraction (Bond Elut jr NH2 (trade name); Varian Inc.)
  9. concentrationThe filtrate was concentrated in vacuo
  10. customthe resultant residue was purified by column chromatography on NH-silica gel (Chromatorex NH silica gel, Solvent: n-hexane/ethyl acetate=100/0 to 95/5)

Sources & evidence

ORD record
ord-2291163570734846beb117ebdfb1d910
Source dataset
uspto-grants-2013_04
Patent number
US08410166B2

Reaction notes

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