Trifluoroacetic acid → HCID 20095127, compound

Temperature

0 °C

A mixture of 12.50 g (38.08 mmol) of 2-(4-iodophenyl)-2-nonene and 6.42 g (55.2 mmol) of triethylsilane was cooled to 0° C. Trifluoroacetic acid (13.03 g, 114.2 mmol) was added dropwise and the resulting mixture was stirred at room temperature for 22 hrs before it was heated to reflux for 30 min. The mixture was cooled and partitioned between 200 ml hexanes and 100 ml of 10% K2CO3 in water. The hexane layer was washed with brine (50 ml) and dried over Na2SO4. The colorless solution was concentrated in vacuo to 12.31 g of a colorless oil The oil was purified by flash chromatography on 370 g of silica gel with hexane as the eluent. Concentration in vacuo afforded 11.45 g (91%) of product as a mobile colorless oil.

1. temperaturewas heated
2. temperatureto reflux for 30 min
3. temperatureThe mixture was cooled
4. custompartitioned between 200 ml hexanes and 100 ml of 10% K2CO3 in water
5. washThe hexane layer was washed with brine (50 ml)
6. dry with materialdried over Na2SO4
7. concentrationThe colorless solution was concentrated in vacuo to 12.31 g of a colorless oil The oil
8. customwas purified by flash chromatography on 370 g of silica gel with hexane as the eluent
9. concentrationConcentration in vacuo

ORD record

ord-39037b0f0f7749dcbd1f08a27d8ec798

Source dataset

uspto-grants-1994_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05308607