Methyl iodide → tert-butyl 2-(1-ethoxy-1-oxopropan-2-yl)-1H-indole-1-carboxylate

HRID 503426ノート

反応式

HRID 503426 の反応式
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[N:7]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH3:2].[CH3:23][Si](C)(C)N[Si](C)(C)C.[K].CI>C1COCC1>[CH2:1]([O:3][C:4](=[O:22])[CH:5]([C:6]1[N:7]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH3:23])[CH3:2]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 45051783Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, potassium saltHCID 53419936tert-Butyl 2-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylate

生成物 1

HCID 59129246tert-butyl 2-(1-ethoxy-1-oxopropan-2-yl)-1H-indole-1-carboxylate収率 89.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

tert-Butyl 2-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylate (3.0 g, 9.9 mmol) was added to anhydrous THF (29 mL) and cooled to −78° C. A 0.5M solution of potassium hexamethyldisilazane (20 mL, 9.9 mmol) was added slowly such that the internal temperature stayed below 60° C. Stirring was continued for 1 h at −78° C. Methyl iodide (727 μL, 11.7 mmol) was added to the mixture. The mixture was stirred for 30 minutes at room temperature. The mixture was quenched with sat. aq. ammonium chloride and partitioned between water and dichloromethane. The aqueous phase was extracted with dichloromethane and the combined organic phases were dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (ethylacetate/hexane=1/9) to give tert-butyl 2-(1-ethoxy-1-oxopropan-2-yl)-1H-indole-1-carboxylate (2.8 g, 88%).

後処理

  1. customstayed below 60° C
  2. stirringThe mixture was stirred for 30 minutes at room temperature
  3. customThe mixture was quenched with sat. aq. ammonium chloride
  4. custompartitioned between water and dichloromethane
  5. extractionThe aqueous phase was extracted with dichloromethane
  6. dry with materialthe combined organic phases were dried over Na2SO4
  7. customevaporated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (ethylacetate/hexane=1/9)

出典と根拠

ORDレコード
ord-a44e33ec6f8c4bb7a4bfb7c6a59ee6a8
出典データセット
uspto-grants-2010_08
特許番号
US07776905B2

反応ノート

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