Iodoethane → HCID 53857432, compound

Temperature

-45 °C

A 500 mL flask was charged with the sodium hydride (0.584 g, 14.61 mmol) and tetrahydrofuran (100 mL). To the resulting suspension was added a solution of EXAMPLE 59A (3.11 g, 11.69 mmol) in tetrahydrofuran (50 mL) dropwise over about 20 minutes and the reaction was stirred for 4 hours under nitrogen. The reaction mixture was cooled to −45° C. and a solution of iodoethane (3.77 mL, 46.8 mmol) in tetrahydrofuran (20 ml) was added dropwise over 20 minutes. The reaction mixture was allowed to come to ambient temperature and stirring was continued for 42 hours. The reaction was diluted with brine (400 mL) and extracted with ether (400 ml, 2×200 mL). The combined organics were dried over sodium sulfate, filtered and concentrated. The crude material was purified on the ISCO chromatography system on a silica gel cartridge (150 g) eluting with a 0, 10, 25, and 50% ethyl acetate/hexane step gradient to give the title compound. MS DCI+) m/e 295 (M+H)+.

1. customto come to ambient temperature
2. stirringstirring
3. waitwas continued for 42 hours
4. extractionextracted with ether (400 ml, 2×200 mL)
5. dry with materialThe combined organics were dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude material was purified on the ISCO chromatography system on a silica gel cartridge (150 g)
9. washeluting with a 0, 10, 25, and 50% ethyl acetate/hexane step gradient

ORD record

ord-6e0c6c4eb77149669a432f51dc437f5e

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08536180B2