Chloroform → HCID 75525756, compound

Temperature

100 °C

To a suspension of 1-adamantanecarboxylic acid (1.50 g) in water (22 mL), sodium carbonate (3.53 g) was added, and the mixture was stirred at 100° C. for 20 minutes. After cooling to 0° C., tetrabutylammonium hydrogen sulfate (1.00 g), chloroform (30 mL) and 1-chloroethyl sulfochloridate (1.94 g) were added to the reaction mixture, and the mixture was stirred at 0° C. for 1 hour and at room temperature for 12 hours. To the reaction solution, water was added, and the mixture was extracted twice with chloroform. The combined organic layer was washed with brine and then dried over anhydrous sodium sulfate. The insoluble was filtered off and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (silica gel cartridge, hexane:ethyl acetate=100:0-50:50) to give 1-chloroethyl adamantane-1-carboxylate (A-2-1, 1.10 g) as a colorless oil.

1. additionwas added
2. temperatureAfter cooling to 0° C.
3. stirringthe mixture was stirred at 0° C. for 1 hour and at room temperature for 12 hours
4. extractionthe mixture was extracted twice with chloroform
5. washThe combined organic layer was washed with brine
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationThe insoluble was filtered off
8. concentrationthe filtrate was concentrated under reduced pressure
9. customThe resulting residue was purified by silica gel column chromatography (silica gel cartridge, hexane:ethyl acetate=100:0-50:50)

ORD record

ord-0532e0d652c54a518ce1eca33d76fc6f

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428483B2