Potassium Carbonate → Methyl 3-methyl-4-(2-methoxy-5-nitrophenoxy)butyrate

HRID 2305629ノート

反応式

HRID 2305629 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[OH:12].Br[CH2:14][CH:15](C)[CH2:16][C:17]([O:19][CH3:20])=[O:18].[C:22](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:14][CH:15]([CH2:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[O:12][CH3:22])[CH2:16][C:17]([O:19][CH3:20])=[O:18]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 767382-Methoxy-4-nitrophenolHCID 14104192Methyl 4-bromo-3-methylbutanoate

生成物 1

HCID 18433387Methyl 3-methyl-4-(2-methoxy-5-nitrophenoxy)butyrate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 2-methoxy-4-nitrophenol (0.207 mg. 1.23 mmole) {Aldrich}, methyl 4-bromo-3-methylbutyrate(0.25 g. 1.35 mmole) and potassium carbonate (0.19 g. 1.35 mmole) in DMF (10 mL.) was heated and stirred at 80° C. for 8 hours. After cooling, the inorganics were filtered off, and the filtrate evaporated to dryness. The residue was dissolved in dichloromethane and washed twice with water. After drying (MgSO4) the solvent was evaporated off to yield an oil. The oil was purified by chromatography (Varian Megabondelut silica column) using a gradient of 100% dichloromethane to 20% ethyl acetate/dichloromethane to give methyl 3-methyl-4-(2-methoxy-5-nitrophenoxy)butyrate as an oil (90 mg. 29%) ms 284(M+)

後処理

  1. temperaturewas heated
  2. temperatureAfter cooling
  3. filtrationthe inorganics were filtered off
  4. customthe filtrate evaporated to dryness
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washwashed twice with water
  7. dry with materialAfter drying (MgSO4) the solvent
  8. customwas evaporated off
  9. customto yield an oil
  10. customThe oil was purified by chromatography (Varian Megabondelut silica column)

出典と根拠

ORDレコード
ord-567cb79db0824821a119fb0e7f4831ce
出典データセット
uspto-grants-2002_08
特許番号
US06441012B1

反応ノート

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