HCID 86662726, compound → HCID 66778125, compound

HRID 2090963Notes

Reaction equation

HRID 2090963 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH:14]=[C:13]([CH:15]=[O:16])[C:12]([CH2:17][CH3:18])=[N:11]2)[CH:7]=[CH:8][CH:9]=1)[CH3:2].[CH2:19]([Mg]Br)[CH:20]([CH3:22])[CH3:21]>O1CCCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH:14]=[C:13]([CH:15]([OH:16])[CH2:19][CH:20]([CH3:22])[CH3:21])[C:12]([CH2:17][CH3:18])=[N:11]2)[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 86662726HCID 86662726, compoundHCID 178418816HCID 178418816, compound

Product 1

HCID 66778125HCID 66778125, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (20 mL) of 1-(3-ethoxyphenyl)-3-ethyl-1H-pyrazole-4-carbaldehyde (1.7 g) synthesized in Example 83(2) in tetrahydrofuran was added dropwise under ice-cooling, isobutylmagnesium bromide (12.0 mL, 1M tetrahydrofuran solution). After the completion of the dropwise addition, the ice bath was removed, and the mixture was stirred at room temperature for 15 min. To the reaction mixture was added aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio) to give the title object compound (1.4 g, 67%) as a pale-yellow oil.

Workup

  1. temperaturecooling
  2. additionAfter the completion of the dropwise addition
  3. customthe ice bath was removed
  4. additionTo the reaction mixture was added aqueous ammonium chloride solution
  5. extractionthe mixture was extracted with ethyl acetate
  6. concentrationThe extract was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio)

Sources & evidence

ORD record
ord-512686782d4549f49d959a504df28f1c
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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