반응 #49865

반응 방정식

water

sodium hydroxide

1,1-dimethylethyl 1-methyl-3(1-methylethoxy)-5-(phenylmethoxy)-1H-indole-2-carboxylate

water

→

product

수율 88.4%

1-Methyl-3-(1-methylethoxy)-5-(phenylmethoxy)-1H-indole-2-carboxylic acid

수율 88.4%

용매

2-methoxyethanol

반응 조건

후처리

1. 1
   온도at reflux for 3 hours
2. 2
   온도cooled
3. 3
   온도The mixture is heated on a hot plate until nearly one phase
4. 4
   여과filtered hot
5. 5
   workup.ADDITIONThe warm filtrate is immediately treated with 50 mL of 4.0N HCl
6. 6
   여과the precipitated solid is filtered
7. 7
   세척washed with 25% methanol in water

실험 절차

A suspension of 1,1-dimethylethyl 1-methyl-3(1-methylethoxy)-5-(phenylmethoxy)-1H-indole-2-carboxylate (5.6 g, 14 mmol) in 80 mL of 2-methoxyethanol is treated with a solution of 50% aqueous sodium hydroxide (5.0 g, 63 mmol) followed by the addition of 15 mL of water. The mixture is stirred at reflux for 3 hours, then cooled and added to 700 mL of water. The mixture is heated on a hot plate until nearly one phase and filtered hot. The warm filtrate is immediately treated with 50 mL of 4.0N HCl. After cooling to room temperature, followed by 1 hour in an ice bath, the precipitated solid is filtered and washed with 25% methanol in water to give 4.2 g (88%) of product suitable for further synthesis. A sample recrystallized from ethyl acetate-hexane has mp 136° C.-dec.

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