Benzyl Alcohol → 5-benzyloxy-N,N-dimethyl-2-nitrobenzamide

HRID 2114177ノート

反応式

HRID 2114177 の反応式
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:12]1[CH:13]=[CH:14][C:15]([N+:23]([O-:25])=[O:24])=[C:16]([CH:22]=1)[C:17]([N:19]([CH3:21])[CH3:20])=[O:18]>CN(C=O)C>[CH2:3]([O:10][C:12]1[CH:13]=[CH:14][C:15]([N+:23]([O-:25])=[O:24])=[C:16]([CH:22]=1)[C:17]([N:19]([CH3:21])[CH3:20])=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 229348075-Chloro-N,N-dimethyl-2-nitrobenzamide

生成物 1

HCID 231302675-benzyloxy-N,N-dimethyl-2-nitrobenzamide収率 89.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

Sodium hydride (210 mg) was suspended in DMF (10 mL), and the suspension was cooled to 0° C. and thereto were added benzyl alcohol (568 mg) and a solution of 5-chloro-N,N-dimethyl-2-nitrobenzamide (1.00 g) in DMF (2 mL). The mixture was stirred at 50° C. for 0.5 hour and then concentrated. The residue was acidified with 2N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2→2:3) to give 5-benzyloxy-N,N-dimethyl-2-nitrobenzamide (1.18 g)

後処理

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2→2:3)

出典と根拠

ORDレコード
ord-fc65824a0cfa40f8a7587440764e6c86
出典データセット
uspto-grants-2008_10
特許番号
US07432392B2

反応ノート

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