Acetone cardice → HCID 178440337, compound

HRID 244945Notes

Reaction equation

HRID 244945 reaction equation
C([O:9][C:10]1[N:14]([C:15]([CH3:24])([CH3:23])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:13]=[C:12]([CH:25]([CH3:27])[CH3:26])[C:11]=1Br)(=O)C1C=CC=CC=1.[CH3:29][C:30]([CH3:32])=O.C(=O)=[O:34].[CH2:36]([Li])[CH2:37][CH2:38][CH3:39]>O1CCCC1.CCCCCC>[OH:9][C:10]1[N:14]([C:15]([CH3:23])([CH3:24])[CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:13]=[C:12]([CH:25]([CH3:26])[CH3:27])[C:11]=1[C:29]([C:30]1[CH:32]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:34]

Participants

6

Reactant 3

HCID 18522661Acetone cardiceHCID 67815312HCID 67815312, compoundHCID 178418339Butyllithium

Product 1

HCID 178440337HCID 178440337, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
72 °C

Procedure

1.60 g (3.63 mmol) of 4-bromo-3-isopropyl-1-(2-methyl-1-phenylpropan-2-yl)-1H-pyrazol-5-yl benzoate was dissolved in 16 mL of tetrahydrofuran and cooled with a coolant (acetone/dry ice) to −60° C., and after dropwise addition of 2.60 ml (4.24 mmol) of 1.63 M n-butyllithium in n-hexane, stirred at 72° C. for 4 hours under a nitrogen atmoephere. The reaction was quenched with distilled water, and the reaction solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (silica gel12 g, ethyl acetate:hexane=1:20) to give 520 mg of the desired product as a yellow oil.

Workup

  1. customThe reaction was quenched with distilled water
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (silica gel12 g, ethyl acetate:hexane=1:20)

Sources & evidence

ORD record
ord-1bc68b47b376400b9b6eddc7cbb0389e
Source dataset
uspto-grants-2014_02
Patent number
US08658686B2

Reaction notes

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