Iodoethane → 1-(4-bromo-2,6-dimethylphenyl)4-(2-ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-1H-pyrazole

HRID 1740109노트

반응식

HRID 1740109 반응식
[H-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([N:11]2[C:15]([CH2:16][CH3:17])=[C:14]([CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21][C:20]=3[OH:29])[C:13]([CH2:30][CH3:31])=[N:12]2)=[C:6]([CH3:32])[CH:5]=1.I[CH2:34][CH3:35]>O1CCCC1>[Br:3][C:4]1[CH:5]=[C:6]([CH3:32])[C:7]([N:11]2[C:15]([CH2:16][CH3:17])=[C:14]([CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21][C:20]=3[O:29][CH2:34][CH3:35])[C:13]([CH2:30][CH3:31])=[N:12]2)=[C:8]([CH3:10])[CH:9]=1

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 537145601-[1-(4-Bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-ylmethyl]-naphthalene-2-ol

생성물 1

HCID 218373011-(4-bromo-2,6-dimethylphenyl)4-(2-ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-1H-pyrazole수율 26.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Sodium hydride (60% mineral oil dispersion, 0.337 g, 8.4 mmol) was added portionwise to a solution of 1-[1-(4-bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-ylmethyl]-naphthalene-2-ol (1.30 g, 8.4 mmol) in 12 ml anhydrous tetrahydrofuran. After stirring 5 minutes, iodoethane (1.12 ml, 14 mmol) was added, and the resulting reaction mixture was stirred 16 hours at ambient temperature. The solvent was removed in vacuo, and the residue was then extracted with methylene chloride/water (25 ml of each). The aqueous phase was twice extracted with 25 ml portions of fresh methylene chloride. The combined organic extracts were dried (anhydrous sodium sulfate), and concentrated in vacuo to an oily solid (1.92 g). Flash chromatography of the entire sample (silica gel, 40 micron mesh; elution with ethyl acetate/hexanes =6:94 in volume) afforded 1.1 g of the title compound as an off white solid.

후처리

  1. customthe resulting reaction mixture
  2. stirringwas stirred 16 hours at ambient temperature
  3. customThe solvent was removed in vacuo
  4. extractionthe residue was then extracted with methylene chloride/water (25 ml of each)
  5. extractionThe aqueous phase was twice extracted with 25 ml portions of fresh methylene chloride
  6. dry with materialThe combined organic extracts were dried (anhydrous sodium sulfate)
  7. concentrationconcentrated in vacuo to an oily solid (1.92 g)
  8. washFlash chromatography of the entire sample (silica gel, 40 micron mesh; elution with ethyl acetate/hexanes =6:94 in volume)

출처 및 근거

ORD 기록
ord-f1b9124a4e1b406fb90a8bee3ae149b2
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05968944

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