HCID 83886996, compound → HCID 66777486, compound

HRID 2090928Notes

Reaction equation

HRID 2090928 reaction equation
[CH:1]1([Mg]Br)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([N:17]2[CH:21]=[C:20]([CH:22]=[O:23])[C:19]([CH3:24])=[N:18]2)[CH:14]=[CH:15][CH:16]=1>O1CCCC1>[CH:1]1([CH:22]([C:20]2[C:19]([CH3:24])=[N:18][N:17]([C:13]3[CH:14]=[CH:15][CH:16]=[C:11]([O:10][CH3:9])[CH:12]=3)[CH:21]=2)[OH:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 83886996HCID 83886996, compound2×HCID 178419651HCID 178419651, compound

Product 1

HCID 66777486HCID 66777486, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (15 mL) of in 1-(3-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbaldehyde (0.62 g) synthesized in the above-mentioned (2) in tetrahydrofuran under ice-cooling was added dropwise cyclohexylmagnesium bromide (4.3 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 (0.60 g, 70%) 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-92c2529d653e4fa19a6a0b8bbbb63202
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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