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

HRID 624066

反応式

HRID 624066 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-37e3e9b30d14439aa2e004f5e331caf0
出典データセット
uspto-grants-2016_04
特許番号
US09303023B2

関連ノート

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