Trifluoroacetic acid → HCID 18615568, compound

Temperature

-50 °C

To a 250-mL flask was added 1-(6-bromo-benzo[1,3]dioxol4-yl)-ethanol (9.3 g, 37.9 mmol) was added. The solid was cooled to −50° C. and trifluoroacetic acid (44 mL, 568 mmol) was added. Followed addition of triethylsilane (60.5 mL, 379 mmol). The mixture was stirred at reflux for 5 hours, and evaporated in vacuo to an oil. The oil was distilled twice, collecting the fraction boiling between 80° C. and 110° C. at 1.5 mm Hg. The oil was chromatographed on 100 g silica gel, eluted with 5:95 ethyl acetate/hexane. Evaporation of the appropriate fractions gave a clear oil, 6.56 g, 75.6% yield. NMR spectra and elemental analysis were consistent with the structure.

1. additionwas added
2. temperatureat reflux for 5 hours
3. customevaporated in vacuo to an oil
4. distillationThe oil was distilled twice
5. customcollecting the fraction
6. customboiling between 80° C. and 110° C. at 1.5 mm Hg
7. customThe oil was chromatographed on 100 g silica gel
8. washeluted with 5:95 ethyl acetate/hexane
9. customEvaporation of the appropriate fractions
10. customgave a clear oil, 6.56 g, 75.6% yield

ORD record

ord-0d87f8d605764d5d950a6f9ac893c51c

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06252070B1