Ozone → HCID 19706767, compound

Temperature

-78 °C

4,4-difluoro-3-ethyl-3-trimethylsilyloxy-5-hexene (2.00 g, 8.88 mmol) was dissolved in dichloromethane (80 ml), and the solution was cooled to -78° C. A gaseous mixture of O3 in O2 was passed into the solution until it became blue. Nitrogen was bubbled through the solution to remove excess ozone, dimethyl sulfide (3 ml) was added, and the solution was brought slowly to room temperature. Following ozonide decomposition, dichloromethane was added, and the organic layer was washed with water (twice), dried over CaCl2 and concentrated under reduced pressure. Flash chromatography (50 g silica gel; 5% EtOAc in petroleum ether as eluant) to give the title compound as a pale yellow oil, δ 0.14 (s 9H), 0.91 (m, 6H), 1.64 (m, 2H), 1.85 (m, 2H), 9.55 (t, 1H).

1. customNitrogen was bubbled through the solution
2. customto remove excess ozone, dimethyl sulfide (3 ml)
3. additionwas added
4. customwas brought slowly to room temperature
5. additionFollowing ozonide decomposition, dichloromethane was added
6. washthe organic layer was washed with water (twice),
7. dry with materialdried over CaCl2
8. concentrationconcentrated under reduced pressure

ORD record

ord-8b8cee90fc9446d68f3921afdcdb9272

Source dataset

uspto-grants-1998_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05710142