Formaldehyde → HCID 11252104, Verbindung

Temperatur

-78 °C

(1R,5S)-6,6-Dimethylbicyclo[3.1.1]heptan-2-one (0.938 mL, 920 mg) was added to tetrahydrofuran (50 mL) and the mixture was cooled to −78° C. using an isopropanol/dry ice bath. Lithium bis(trimethylsilyl)amide (1M in tetrahydrofuran, 7.99 mL) was added, and the solution was stirred at −78° C. for 15 minutes. The solution was allowed to warm to 0° C. in a water/ice bath and the mixture was stirred for 45 minutes. Paraformaldehyde (2000 mg) was added. The solution was stirred at 0° C. for 15 minutes, allowed to warm to room temperature and stir for an additional four hours. The reaction was quenched with saturated aqueous ammonium chloride, extracted with diethyl ether, washed with brine, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by flash column chromatography on silica gel using 5% ethyl acetate in hexanes.

1. temperatureto warm to 0° C. in a water/ice bath
2. stirringthe mixture was stirred for 45 minutes
3. stirringThe solution was stirred at 0° C. for 15 minutes
4. temperatureto warm to room temperature
5. stirringstir for an additional four hours
6. customThe reaction was quenched with saturated aqueous ammonium chloride
7. extractionextracted with diethyl ether
8. washwashed with brine
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated
12. custompurified by flash column chromatography on silica gel using 5% ethyl acetate in hexanes

ORD-Eintrag

ord-ea5b04e5be2a42f4b8477dbb2cedaf66

Quelldatensatz

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08188077B2