2-Ethylbutyraldehyde → 2-ethyl-1-[1-(4-methoxybenzyl)-1H-pyrazol-5-yl]butan-1-ol

HRID 2243115노트

반응식

HRID 2243115 반응식
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([CH2:7][N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)=[CH:5][CH:4]=1.[Li]CCCC.[CH2:20]([CH:22]([CH2:25][CH3:26])[CH:23]=[O:24])[CH3:21]>C1COCC1>[CH2:20]([CH:22]([CH2:25][CH3:26])[CH:23]([C:12]1[N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:14][CH:13]=2)[N:9]=[CH:10][CH:11]=1)[OH:24])[CH3:21]

참가 물질

5

반응물 3

HCID 73592-EthylbutyraldehydeHCID 102417081-(4-Methoxybenzyl)-1H-pyrazoleHCID 178418339Butyllithium

생성물 1

HCID 685942442-ethyl-1-[1-(4-methoxybenzyl)-1H-pyrazol-5-yl]butan-1-ol수율 44.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To 1-(4-methoxybenzyl)-1H-pyrazole (Synthetic Comm. 25(5), 761-774 (1995)) (2.43 g, 12.9 mmol) in THF (100 mL) at −78° C. was added a solution of n-BuLi (2 M in cyclohexane, 7.1 mL, 14.2 mmol) dropwise. After 75 min, 2-ethylbutyraldehyde (1.3 mL, 10.6 mmol) was added. After 45 min the reaction mixture was quenched with saturated aqueous ammonium chloride (50 mL), extracted with EtOAc (3×100 mL), dried (Na2SO4) and concentrated. Column chromatography (EtOAc/hexanes, 1:4) provided 1.37 g (37%) of 2-ethyl-1-[1-(4-methoxybenzyl)-1H-pyrazol-5-yl]butan-1-ol as an oil.

후처리

  1. customAfter 45 min the reaction mixture was quenched with saturated aqueous ammonium chloride (50 mL)
  2. extractionextracted with EtOAc (3×100 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-39268beb2fdb4f1fb2419b25c4f578c2
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07674813B2

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