Hydrochloric Acid → HCID 67198944, compound

Temperature

-78 °C

A dichloromethane solution (80 mL) of oxalyl chloride (1.88 mL, 22.5 mmol) was cooled to −78° C., and a dichloromethane solution (20 mL) of dimethyl sulfoxide (3.0 mL, 43.0 mmol) was added dropwise thereto. The mixture was stirred at −78° C. for 10 minutes. Then, a dichloromethane solution (20 mL) of (1-vinylcyclobutyl)ethanol (1.94 g, 15 mmol) was added dropwise thereto, and the mixture was further stirred at −78° C. for 3 hours. Triethylamine (8 mL, 60 mmol) was added thereto, and the mixture was gradually brought to room temperature and then stirred for 1 hour. 1 N hydrochloric acid and saturated saline were added thereto, followed by extraction with dichloromethane. The organic layer was washed with saturated saline and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was dissolved in tetrahydrofuran (40 mL). To the solution, trimethylboron (6.2 mL) and zinc powder (4.46 g) were added, and methyl bromoacetate (4.2 mL, 44.1 mmol) was then added dropwise thereto. After stirring at room temperature for 30 minutes, the reaction solution was heated to 40° C. and stirred for 20 minutes. The mixture was further brought to room temperature and stirred for 1 hour, and glycerol, water, and saturated saline were then added thereto, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography to obtain the compound of interest as a colorless oil substance (1.22 g, 40%).

1. stirringthe mixture was further stirred at −78° C. for 3 hours
2. customwas gradually brought to room temperature
3. stirringstirred for 1 hour
4. extractionfollowed by extraction with dichloromethane
5. washThe organic layer was washed with saturated saline
6. dry with materialdried over anhydrous sodium sulfate
7. distillationthe solvent was distilled off under reduced pressure
8. dissolutionThe residue was dissolved in tetrahydrofuran (40 mL)
9. additionTo the solution, trimethylboron (6.2 mL) and zinc powder (4.46 g) were added
10. stirringAfter stirring at room temperature for 30 minutes
11. temperaturethe reaction solution was heated to 40° C.
12. stirringstirred for 20 minutes
13. customwas further brought to room temperature
14. stirringstirred for 1 hour
15. extractionfollowed by extraction with ethyl acetate
16. washThe organic layer was washed with saturated saline
17. dry with materialdried over anhydrous sodium sulfate
18. distillationthe solvent was distilled off under reduced pressure
19. customThe residue was purified by column chromatography
20. customto obtain the compound of interest as a colorless oil substance (1.22 g, 40%)

ORD record

ord-0260a2604f454567ad5cc5512efdfb74

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947738B2