Sulfuric Acid → HCID 21906966, Verbindung

Temperatur

0 °C

A mixture of 1-phenylcyclobutanecarboxylic acid (10) and acetic acid (20 ml) and H2SO4 (20 ml) and KNO3 (1.1 eq) was stirred at 0° C. for 20 min. The mixture was warmed to RT and stirred overnight. The mixture was poured on ice and stirred until all ice melted. The precipitate was filtered and used for next step without further purification. The above product (5 g) was dissolved into THF and stirred at 0° C., NaBH4 (3 eq) was added slowly to the reaction followed by slowly addition of BF3.Et2O (3 eq). The reaction was stirred at RT overnight and quenched with 1 N NaOH slowly until bubble ceased. The solution was extracted with EtOAc and washed with H2O followed by brine, dried over Na2SO4 and evaporated. The residue was purified by column chromatography to give [(4-nitrophenyl)cyclobutyl]methane-1-ol as an oil.

1. temperatureThe mixture was warmed to RT
2. stirringstirred overnight
3. additionThe mixture was poured on ice
4. stirringstirred until all ice
5. filtrationThe precipitate was filtered
6. customused for next step without further purification
7. dissolutionThe above product (5 g) was dissolved into THF
8. stirringstirred at 0° C.
9. stirringThe reaction was stirred at RT overnight
10. customquenched with 1 N NaOH slowly
11. customuntil bubble
12. extractionThe solution was extracted with EtOAc
13. washwashed with H2O
14. dry with materialdried over Na2SO4
15. customevaporated
16. customThe residue was purified by column chromatography

ORD-Eintrag

ord-fb4db718258847b8ab10cea653cd66ad

Quelldatensatz

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07129252B2