反応 #1266101

反応方程式

EtOAc—H2O

potassium tert butoxide

3-isopropyl indole

4-chlorosulfonyl benzoic acid methyl ester

→

title compound

収率 51.2%

4-(3-Isopropyl-indole-1-sulfonyl)-benzoic acid methyl ester

収率 51.2%

溶媒

DMF

hexane EtOAc

反応条件

後処理

1. 1
   workup.STIRRINGStir the resulting yellow solution overnight
2. 2
   その他Separate the EtOAc
3. 3
   抽出sequentially extract with H2O (3×250 mL)
4. 4
   洗浄wash with brine
5. 5
   乾燥dry (MgSO4)
6. 6
   ろ過filter
7. 7
   その他evaporate
8. 8
   その他giving 0.38 g

実験手順

Add potassium tert butoxide 1.0 M (1.6 mL, 0.0016 mol) dropwise to a stirring solution of 3-isopropyl indole (0.217 g, 0.00136 mol) in dry DMF (20 mL) under N2 at ambient temperature. Stir the reaction mixture for 30 minutes and add portionwise 4-chlorosulfonyl benzoic acid methyl ester (0.328 g, 0.0014 mol). The light brown reaction mixture decolorizes immediately. Stir the resulting yellow solution overnight. Pour into a EtOAc—H2O mixture (100 to 300 mL). Separate the EtOAc and sequentially extract with H2O (3×250 mL), wash with brine, dry (MgSO4), filter and evaporate giving 0.38 g. Chromatograph on the ISCO using a gradient hexane-EtOAc (0-50%, 30 30 minutes) to give 0.249 g (51%) of the title compound as a waxy solid. Mass spectrum (m/e) (M+H) 358.1113. found (M+H) 358.1129.

出典