Tetrahydrofuran → HCID 178440337, compound

HRID 1504284Notes

Reaction equation

HRID 1504284 reaction equation
Br[C:2]1[C:3]([CH:26]([CH3:28])[CH3:27])=[N:4][N:5]([C:16]([CH3:25])([CH3:24])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:6]=1C1C=CC=CC=1C([O-])=O.[CH3:29][C:30]([CH3:32])=O.C(=O)=[O:34].C([Li])CCC.[O:41]1[CH2:45][CH2:44][CH2:43][CH2:42]1>CCCCCC>[OH:34][C:6]1[N:5]([C:16]([CH3:25])([CH3:24])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:4]=[C:3]([CH:26]([CH3:28])[CH3:27])[C:2]=1[C:45]([C:44]1[CH:32]=[CH:30][CH:29]=[CH:42][CH:43]=1)=[O:41]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 18522661Acetone cardiceHCID 86711161HCID 86711161, compoundHCID 178418339Butyllithium

Product 1

HCID 178440337HCID 178440337, compound

Reagents, catalysts & solvents 1

HCID 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-ylbenzoate 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 atmosphere. 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 gel 12 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 gel 12 g, ethyl acetate:hexane=1:20)

Sources & evidence

ORD record
ord-27f2c767612e4e3c92af00f8e38351e8
Source dataset
uspto-grants-2015_12
Patent number
US09212348B2

Reaction notes

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