2-Ethylbutyraldehyde → 2-ethyl-1-{1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-5-yl}butan-1-ol

HRID 748043Notes

Reaction equation

HRID 748043 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:15]=[CH:14][CH:13]=[N:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([Li])(C)(C)C.[CH2:21]([CH:23]([CH2:26][CH3:27])[CH:24]=[O:25])[CH3:22]>C1COCC1>[CH2:21]([CH:23]([CH2:26][CH3:27])[CH:24]([C:15]1[N:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[N:12]=[CH:13][CH:14]=1)[OH:25])[CH3:22]

Participants

5

Reactant 3

HCID 73592-EthylbutyraldehydeHCID 3207501-TosylpyrozoleHCID 178418306HCID 178418306, compound

Product 1

HCID 685938962-ethyl-1-{1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-5-yl}butan-1-olYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1-[(4-methylphenyl)sulfonyl]-1H-pyrazole (0.50 g, 2.26 mmol) [J. Chem. Res., Synopses, 10, 327 (1979)] in THF (23 mL) at −78° C. was added a solution of t-butyllithium (1.7 M in pentane, 1.5 mL, 2.49 mmol) dropwise. After 10 min 2-ethylbutyraldehyde (0.31 mL, 2.49 mmol) was added. After 10 min the reaction mixture was quenched with saturated aqueous ammonium chloride (5 mL) and then diluted with H2O (30 mL) and extracted with EtOAc (3×30 mL). The organic extract was dried (Na2SO4) and concentrated. The residue was purified by column chromatography (EtOAc/hexane, 3:7) to give 0.546 g (75%) of 2-ethyl-1-{1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-5-yl}butan-1-ol.

Workup

  1. customAfter 10 min the reaction mixture was quenched with saturated aqueous ammonium chloride (5 mL)
  2. additiondiluted with H2O (30 mL)
  3. extractionextracted with EtOAc (3×30 mL)
  4. extractionThe organic extract
  5. dry with materialwas dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (EtOAc/hexane, 3:7)

Sources & evidence

ORD record
ord-d1886f497bab46c1aab4a1be25c8ce8f
Source dataset
uspto-grants-2008_07
Patent number
US07399778B2

Reaction notes

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