HCID 86662725, compound → HCID 66777675, compound

HRID 2090955Notes

Reaction equation

HRID 2090955 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]2[CH:13]=[C:12]([CH:14]=[O:15])[C:11]([CH:16]([CH3:18])[CH3:17])=[N:10]2)[CH:6]=[CH:7][CH:8]=1.[CH:19]1([Mg]Br)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>O1CCCC1>[CH:19]1([CH:14]([C:12]2[C:11]([CH:16]([CH3:18])[CH3:17])=[N:10][N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:13]=2)[OH:15])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 86662725HCID 86662725, compound2×HCID 178419651HCID 178419651, compound

Product 1

HCID 66777675HCID 66777675, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (20 mL) of 1-(3-methoxyphenyl)-3-(propan-2-yl)-1H-pyrazole-4-carbaldehyde (2.6 g) synthesized in the above-mentioned (2) in tetrahydrofuran was added dropwise cyclohexylmagnesium bromide (15.0 mL, 1M tetrahydrofuran solution) under ice-cooling. 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 to give a crude product (2.6 g, 75%) of the title object compound 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

Sources & evidence

ORD record
ord-9dc5c8e27dc94cf0871900c61f8a6bee
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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