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

HRID 1404003노트

반응식

HRID 1404003 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-b6d53d3658794be2a8013fe1fcfcf27b
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912199B2

반응 노트

불러오는 중…