Dimethyl Sulfoxide → HCID 86646144, compound

Temperature

-78 °C

Dimethyl sulfoxide (4.71 mL, 66.3 mmol) was added to a methylene chloride solution (70 mL) of oxalyl chloride (2.84 mL, 33.2 mmol) with stirring at −78° C., and the mixture was stirred at this temperature for 5 minutes. Then, a methylene chloride solution (30 mL) of 2-({[tert-butyl(dimethyl)silyl]oxy}methyl)pent-4-en-1-ol (J. Chem. Soc., Perkin Trans. 1 1991, 2073) (5.10 g, 22.1 mmol) was added thereto. The mixture was stirred at this temperature for 15 minutes. Then, triethylamine (12.3 mL, 88.4 mmol) was added thereto, and the mixture was heated to room temperature and stirred. The mixture was separated into aqueous and organic layers by the addition of 0.1 M hydrochloric acid. The organic layer was washed with 0.1 M hydrochloric acid, water, and saturated saline and then dried over anhydrous magnesium sulfate. The residue was filtered and concentrated under reduced pressure, and the obtained residue was dissolved in toluene (50 mL). To the solution, (methoxycarbonylmethylene)triphenylphosphorane (11.1 g, 33.2 mmol) was added, and the mixture was stirred at room temperature for 4 hours and further stirred at 60° C. for 2 hours. The reaction solution was concentrated under reduced pressure, then filtered through Celite, and concentrated again under reduced pressure. Then, the obtained crude product was purified by silica gel column chromatography to obtain the compound of interest as an oil substance (5.69 g, 91%).

1. stirringthe mixture was stirred at this temperature for 5 minutes
2. stirringThe mixture was stirred at this temperature for 15 minutes
3. temperaturethe mixture was heated to room temperature
4. stirringstirred
5. customThe mixture was separated into aqueous and organic layers
6. additionby the addition of 0.1 M hydrochloric acid
7. washThe organic layer was washed with 0.1 M hydrochloric acid, water, and saturated saline
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationThe residue was filtered
10. concentrationconcentrated under reduced pressure
11. dissolutionthe obtained residue was dissolved in toluene (50 mL)
12. stirringthe mixture was stirred at room temperature for 4 hours
13. stirringfurther stirred at 60° C. for 2 hours
14. concentrationThe reaction solution was concentrated under reduced pressure
15. filtrationfiltered through Celite
16. concentrationconcentrated again under reduced pressure
17. customThen, the obtained crude product
18. customwas purified by silica gel column chromatography
19. customto obtain the compound of interest as an oil substance (5.69 g, 91%)

ORD record

ord-17144bd4f1214a56aa93d2a9a4388dcb

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947738B2