Ethylene Oxide → HCID 21875345, compound

To a solution of 2-butylfuran (3.00 g, 24.2 mmol) in THF (24 mL) at −78° C. was added n-BuLi (11.6 mL, 2.5 M, 29.0 mmol) dropwise over 10 min. The reaction was warmed to rt and stirred for 3.5 h. After cooling to 0° C., ethylene oxide (1.81 mL, 36.2 mmol) was added, the reaction was warmed to rt and stirring was continued for 19 h. The reaction was then cooled to 0° C. and quenched with sat. NH4Cl (20 mL), followed by extraction with diethyl ether (2×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give 4.07 g (100%) compound 502A as a bright orange oil. This material was used without further purification. HPLC: 96% at 3.23 min (retention time) (YMC Combiscreen ODS-A column, 4.6×50 mm, eluting with 10–90% aqueous methanol containing 0.2% phosphoric acid over 4 min, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 169.22 [M+H]+.

1. temperatureAfter cooling to 0° C.
2. temperaturethe reaction was warmed to rt
3. stirringstirring
4. waitwas continued for 19 h
5. temperatureThe reaction was then cooled to 0° C.
6. customquenched with sat. NH4Cl (20 mL)
7. extractionfollowed by extraction with diethyl ether (2×50 mL)
8. washThe combined organic layers were washed with brine
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-c66282e91e4640f7a5a4798eede8fd8c

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07141578B2