Реакция #50786

Уравнение реакции

2-(carbomethoxy)-2-(4-methoxybenzylthio)indan

potassium hydroxide

→

2-carboxy-2-(4-methoxybenzylthio)indan

Выход 43.0%

Растворители

ethanol

water

tetrahydrofuran

Условия реакции

Обработка

1. 1
   ФильтрацияFilter
2. 2
   Другоеevaporate the solvent in vacuo
3. 3
   ДругоеPartition between water (125 mL) and ether (75 mL)
4. 4
   ДругоеSeparate the aqueous phase
5. 5
   ЭкстракцияExtract with methylene chloride (75 mL)
6. 6
   Сушкаdry (Na2SO4)
7. 7
   Другоеevaporate the solvent in vacuo
8. 8
   ДругоеPurify by silica gel chromatography (2:1 hexane/ethyl acetate)

Методика

Dissolve 2-(carbomethoxy)-2-(4-methoxybenzylthio)indan (2.20 g, 3.55 mmol) in 95% ethanol (25 mL), water (12 mL) and tetrahydrofuran (15 mL). Treat with potassium hydroxide (1.3 g, 23 mmol) and stir at room temperature for 1 hour. Filter and evaporate the solvent in vacuo. Partition between water (125 mL) and ether (75 mL). Separate the aqueous phase and acidify with cold concentrated hydrochloric acid. Extract with methylene chloride (75 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography (2:1 hexane/ethyl acetate) to give 2-carboxy-2-(4-methoxybenzylthio)indan as a yellow solid (0.48 g).

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