Tetrahydrofuran → HCID 86618039, compound

Lithium (39.4 mg, 5.62 mmol) was added to a THF (25 ml) solution of di-tert-butyldiphenyl (1.87 g, 7.02 mmol) while ice cooling and the reaction solution was stirred at room temperature for three hours. The reaction solution turned dark green during stirring. This solution was added dropwise to THF (5 ml) solution of {[(1S,2S,3E,6S)-7-benzyloxy-1-ethyl-2,6-dimethylhept-3-en-1-yl]oxy}(triethyl)silane (500 mg, 1.28 mmol) slowly (at such a rate that green of the reaction solution was maintained) cooled to −78° C. under stirring. After the reaction solution was stirred at the same temperature for three hours, a saturated ammonium chloride aqueous solution was added thereto and the mixture was warmed to room temperature. After the reaction solution was diluted with ethyl acetate, it was washed with brine. After the organic layer was dried over anhydrous sodium sulfate and the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Merck, commercial name Silica Gel 60, 230-400 mesh; hexane:ethyl acetate=15:1) to obtain the title compound (296 mg) as a colorless oil.

1. stirringduring stirring
2. temperaturewas maintained)
3. temperaturecooled to −78° C.
4. stirringunder stirring
5. stirringAfter the reaction solution was stirred at the same temperature for three hours
6. temperaturethe mixture was warmed to room temperature
7. washwas washed with brine
8. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
9. filtrationthe drying agent was filtered off
10. concentrationthe organic layer was concentrated under reduced pressure
11. customThe obtained residue was purified by silica gel column chromatography (Merck, commercial name Silica Gel 60, 230-400 mesh; hexane:ethyl acetate=15:1)

ORD record

ord-8f789fa78f884127bb1bbb49c2ea2ef7

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07816401B2