Tetrabutylammonium Fluoride → HCID 86753618, compound

Compound 18E (23 mg, 0.0245 mmol) was dissolved in 2 ml of THF and 60 μl (0.060 mmol) of a 1M solution of nBu4NF in THF was added thereto at room temperature. After stirring for 30 minutes, the reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over Glauber's salt and concentrated under reduced pressure. Then the resulting residue was dissolved in 2.3 ml of THF and 100 μl of 12M hydrochloric acid was added thereto. The reaction mixture was stirred at room temperature for 1 hour and then neutralized with sodium hydrogencarbonate. After concentration, the residue was dissolved in ethanol-chloroform (1:5) and the salt was filtered off. The resulting product was purified by silica gel column chromatography (2 g of K-60 manufactured by Katayama Kagaku, eluent; methanol:chloroform=1:5). Thus 15 mg of compound 19E was obtained (yield: 99%). The properties of compound 19E were as follows.

1. customat room temperature
2. washwashed with water
3. dry with materialThe organic layer was dried over Glauber's salt
4. concentrationconcentrated under reduced pressure
5. dissolutionThen the resulting residue was dissolved in 2.3 ml of THF
6. addition100 μl of 12M hydrochloric acid was added
7. stirringThe reaction mixture was stirred at room temperature for 1 hour
8. concentrationAfter concentration
9. dissolutionthe residue was dissolved in ethanol-chloroform (1:5)
10. filtrationthe salt was filtered off
11. customThe resulting product was purified by silica gel column chromatography (2 g of

ORD record

ord-0d6c998939fb4b20862b52ff13a1a428

Source dataset

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05861520