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

HRID 748043

반응식

HRID 748043 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d1886f497bab46c1aab4a1be25c8ce8f
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399778B2

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