聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 1-(苯并[D][1,3]二氧杂环戊烯-5-基)环丙烷甲酸

温度

70 °C

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 24 hours and was then heated at 130° C. for 48 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 was 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 2.37 minutes. 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).

1. temperaturewas then heated at 130° C. for 48 hours
2. extractionextracted once with an equal volume of ethyl acetate and once with an equal volume of dichloromethane
3. filtrationthe precipitate was filtered
4. washwashed with 1 M hydrochloric acid
5. dissolutionThe solid material was dissolved in dichloromethane (400 mL)
6. extractionextracted twice with equal volumes of 1 M hydrochloric acid and once with a saturated aqueous solution of sodium chloride
7. dry with materialThe organic solution was dried over sodium sulfate
8. customevaporated to dryness

ORD记录

ord-5c55747a863342d49769158ec43211dd

来源数据集

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

专利号

US08524767B2