Реакция #46176
ord-16c41d8ea400486091d9c5dbdaba818c
Уравнение реакции
Реагенты
Условия реакции
Обработка
- 1Температураheated at 130° C. for 24 hours
- 2Экстракцияextracted once with an equal volume of ethyl acetate and once with an equal volume of dichloromethane
- 3Фильтрацияthe precipitate filtered
- 4Промывкаwashed with 1 M hydrochloric acid
- 5workup.DISSOLUTIONThe solid material was dissolved in dichloromethane (400 mL)
- 6Экстракцияextracted twice with equal volumes of 1 M hydrochloric acid and once with a saturated aqueous solution of sodium chloride
- 7СушкаThe organic solution was dried over sodium sulfate
- 8Другоеevaporated to dryness
Методика
A mixture of benzo[1,3]dioxole-5-acetonitrile (5.10 g, 31.7 mmol), 1-bromo-2-chloro-ethane (9.00 mL, 109 mmol), and benzyltriethylammonium chloride (0.181 g, 0.795 mmol) was heated at 70° C. and then 50% (wt./wt.) aqueous sodium hydroxide (26 mL) was slowly added to the mixture. The reaction was stirred at 70° C. for 18 hours and then heated at 130° C. for 24 hours. The dark brown reaction mixture was diluted with water (400 mL) and extracted once with an equal volume of ethyl acetate and once with an equal volume of dichloromethane. The basic aqueous solution was acidified with concentrated hydrochloric acid to pH less than one and the precipitate filtered and washed with 1 M hydrochloric acid. The solid material was dissolved in dichloromethane (400 mL) and extracted twice with equal volumes of 1 M hydrochloric acid and once with a saturated aqueous solution of sodium chloride. The organic solution was dried over sodium sulfate and evaporated to dryness to give a white to slightly off-white solid (5.23 g, 80%) ESI-MS m/z calc. 206.1. found 207.1 (M+1)+. Retention time of 2.37 minutes. 1H NMR (400 MHz, DMSO-d6) δ 1.07-1.11 (m, 2H), 1.38-1.42 (m, 2H), 5.98 (s, 2H), 6.79 (m, 2H), 6.88 (m, 1H), 12.26 (s, 1H).