Iodoethane → 2-(2-Bromo-5-methoxy-phenyl)-2-ethyl-butyric acid

HRID 61926

反応式

HRID 61926 の反応式
C[O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[Br:13].[H-].[Na+].[CH2:17]1OCCOCCOCCOCCO[CH2:18]1.[CH2:32](I)[CH3:33]>CN(C=O)C.C(OCC)(=O)C>[Br:13][C:6]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=1[C:4]([CH2:32][CH3:33])([CH2:17][CH3:18])[C:3]([OH:2])=[O:14]

参加物

7

反応物 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 10658910Methyl (2-bromo-5-methoxyphenyl)acetate

生成物 1

HCID 668353562-(2-Bromo-5-methoxy-phenyl)-2-ethyl-butyric acid

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
140 °C

実験手順

(2-Bromo-5-methoxy-phenyl)-acetic acid methyl ester (3.51 g, 13.5 mmol) was dissolved in DMF (4.5 ml), and added with NaH (2.1 g, 67.7 mmol). Subsequently, 15-crown-5 (1.38 ml, 6.8 mmol) and EtI (5.5 ml, 67.7 mmol) cooled to 0° C. were added to the mixture. The mixture was diluted with ethyl acetate and washed with water and saturated brine. The residues obtained after concentration under reduced pressure were purified by silica gel column (hexane-ethyl acetate). Then, the resultant was dissolved in ethanol (80 ml) and water (80 ml), added with KOH (91 g), and stirred at 140° C. The reaction solution was extracted with ethyl acetate, and washed with water and saturated brine. After concentration under reduced pressure, the target compound was obtained (10.62 g, 78%).

後処理

  1. additionwere added to the mixture
  2. washwashed with water and saturated brine
  3. customThe residues obtained
  4. concentrationafter concentration under reduced pressure
  5. customwere purified by silica gel column (hexane-ethyl acetate)
  6. dissolutionThen, the resultant was dissolved in ethanol (80 ml)
  7. additionwater (80 ml), added with KOH (91 g)
  8. extractionThe reaction solution was extracted with ethyl acetate
  9. washwashed with water and saturated brine
  10. concentrationAfter concentration under reduced pressure
  11. customthe target compound was obtained (10.62 g, 78%)

出典と根拠

ORDレコード
ord-d12d0702602249d3b4e6de3021d0b768
出典データセット
uspto-grants-2016_09
特許番号
US09440922B2

関連ノート

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