Cesium carbonate → 2-(3,5-dimethyl-4-nitro-1H-pyrazol-1-yl)ethanol

HRID 624066

반응식

HRID 624066 반응식
[CH3:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[C:5]([CH3:10])[NH:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:18][CH2:19][OH:20]>CC#N.C(Cl)Cl>[CH3:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[C:5]([CH3:10])[N:4]([CH2:18][CH2:19][OH:20])[N:3]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 1461723,5-Dimethyl-4-nitropyrazole

생성물 1

HCID 196169562-(3,5-dimethyl-4-nitro-1H-pyrazol-1-yl)ethanol

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

반응 조건

온도
90 °C

실험 절차

To a solution of 3,5-dimethyl-4-nitro-1H-pyrazole (500 mg, 3.52 mmol) in MeCN (5 mL), Cs2CO3 (1.26 g, 3.87 mmol) and 2-bromoethanol (0.3 mL, 4.21 mmol) was added. The resulting mixture was refluxed (90° C.) for 3 h, then the reaction mixture was allowed to reach rt. The mixture was diluted with DCM, filtered, the filter cake rinsed with DCM and the filtrate concentrated in vacuo. The residue was partitionned between water and EtOAc, the org. layer was separated and the aq. layer was extracted with EtOAc (1×). The combined org. layers were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to yield 2-(3,5-dimethyl-4-nitro-1H-pyrazol-1-yl)ethanol as a white solid. LC-MS conditions A: tR=0.53 min, [M+H]+=186.39.

후처리

  1. customto reach rt
  2. filtrationfiltered
  3. washthe filter cake rinsed with DCM
  4. concentrationthe filtrate concentrated in vacuo
  5. customlayer was separated
  6. extractionthe aq. layer was extracted with EtOAc (1×)
  7. washlayers were washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-37e3e9b30d14439aa2e004f5e331caf0
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303023B2

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