Methyl iodide → Methyl 3-(methoxymethyl)-1H-indole-5-carboxylate

HRID 1015441ノート

反応式

HRID 1015441 の反応式
[OH:1][CH2:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[NH:5][CH:4]=1.[CH3:16]I>C(#N)C.[Ag]=O>[CH3:16][O:1][CH2:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[NH:5][CH:4]=1

参加物

5

反応物 2

HCID 6328Methyl iodide2 回HCID 67300394Methyl 3-(hydroxymethyl)-1H-indole-5-carboxylate

生成物 1

HCID 67300506Methyl 3-(methoxymethyl)-1H-indole-5-carboxylate

試薬・触媒・溶媒 2

HCID 92152Silver(II) oxide触媒3 回HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

A 327 mg portion of methyl 3-(hydroxymethyl)-1H-indole-5-carboxylate was dissolved in 9 ml of acetonitrile, mixed with 385 mg of silver oxide and 3.6 ml of methyl iodide and stirred at 80° C. for 5 hours. A 385 mg portion of silver oxide was further added thereto and stirred overnight at 80° C. A 385 mg portion of silver oxide and 3.6 ml of methyl iodide were further added thereto and stirred at 80° C. for 9 hours. After cooling to room temperature, the insoluble matter was removed, the solvent was evaporated, and then the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:6 to 1:5 to 1:4) to obtain 143 mg of methyl 3-(methoxymethyl)-1H-indole-5-carboxylate as a pale yellow solid.

後処理

  1. stirringstirred overnight at 80° C
  2. stirringstirred at 80° C. for 9 hours
  3. temperatureAfter cooling to room temperature
  4. customthe insoluble matter was removed
  5. customthe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:6 to 1:5 to 1:4)

出典と根拠

ORDレコード
ord-71d787d2a80b42b096f37d813ecec770
出典データセット
uspto-grants-2011_07
特許番号
US07985764B2

反応ノート

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