Benzyl Chloride → Ethyl 1-benzyl-5-chloroindole-2-carboxylate

HRID 2104394ノート

反応式

HRID 2104394 の反応式
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 78518Ethyl 5-chloroindole-2-carboxylate

生成物 1

HCID 13295699Ethyl 1-benzyl-5-chloroindole-2-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

5-Chloroindole-2-carboxylic acid ethyl ester (1.4 g) was dissolved in N,N-dimethylformamide (30 mL), and to the solution were added potassium carbonate (2.9 g) and benzyl chloride (2.4 mL), followed by stirring in a bath at a temperature of 100° C. for 1.5 hours. The reaction mixture was concentrated, and the residue was poured into ice water. The thus-obtained mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and was dried over sodium sulfate anhydrate. The solvent was distilled away, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19). The thus-obtained compound was crystallized from diethyl ether-hexane, to thereby give the title compound (1.6 g).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was poured into ice water
  3. extractionThe thus-obtained mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialwas dried over sodium sulfate anhydrate
  6. distillationThe solvent was distilled away
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19)
  8. customThe thus-obtained compound was crystallized from diethyl ether-hexane

出典と根拠

ORDレコード
ord-df33cd28ef834a67829048bf6b48c6f6
出典データセット
uspto-grants-2009_08
特許番号
US07576135B2

反応ノート

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