反応 #3435

反応方程式

4-Hydroxy-2-methyl-1-(phenylmethyl)-1H-indole

NaH

methyl bromoacetate

→

[[2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester

収率 88.0%

溶媒

DMF

water

反応条件

後処理

1. 1
   workup.STIRRINGstirring
2. 2
   温度maintained for 17 hours
3. 3
   抽出extracted with ethyl acetate
4. 4
   洗浄The ethyl acetate solution was washed with brine
5. 5
   乾燥dried (MgSO4)
6. 6
   濃縮concentrated at reduced pressure
7. 7
   その他The residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

実験手順

4-Hydroxy-2-methyl-1-(phenylmethyl)-1H-indole (530 mg, 2.2 mmol) was added to 88 mg (2.2 mmol) of 60% NaH/mineral oil in 20 mL of DMF and the mixture stirred for 0.67 hours. Then, 0.21 mL (2.2 mmol) of methyl bromoacetate was added and stirring maintained for 17 hours. The mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried (MgSO4), and concentrated at reduced pressure. The residue was chromatographed on silica gel eluting with 20% EtOAc/hexane to give 597 mg (88% yield) of [[2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester, 140°-143° C.

出典