Methyl iodide → Methyl 2-(4-nitrophenyl)propionate

HRID 272742ノート

反応式

HRID 272742 の反応式
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[CH2:15]1OCCOCCOCCOCCOCCOC1.CI.[H-].[Na+]>CN(C=O)C>[N+:11]([C:8]1[CH:7]=[CH:6][C:5]([CH:4]([CH3:15])[C:3]([O:2][CH3:1])=[O:14])=[CH:10][CH:9]=1)([O-:13])=[O:12]

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2855718-Crown-6HCID 270191Methyl p-nitrophenylacetate

生成物 1

HCID 3016521Methyl 2-(4-nitrophenyl)propionate収率 697.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

A mixture of (4-nitro-phenyl)-acetic acid methyl ester (3.0 g, 15 mmol), 18-crown-6 (396 mg, 1.5 mmol), and methyl iodide (3.74 mL, 60 mmol) were combined in DMF (50 mL) and cooled to 0° C. Sodium hydride (660 mg, 16.5 mmol) was added. The solution was stirred with warming to room temperature overnight. The solution was partitioned between ethyl acetate and water. The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated under vacuum to provide 2.19 g (70%) of the title compound. MS (DCI) m/e 210 (M+H)+.

後処理

  1. temperaturewith warming to room temperature overnight
  2. customThe solution was partitioned between ethyl acetate and water
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-d66c2f07b1af4951828b9ae4129239f5
出典データセット
uspto-grants-2008_11
特許番号
US07456169B2

反応ノート

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