Dimethyl Sulfoxide → Bicyclo[2.2.1]heptane-7-carbaldehyde

Temperatur

-78 °C

In a flask under argon was placed dichloromethane (10 mL) and a 2M solution of oxalyl chloride in dichloromethane (1.43 mL, 2.85 mmol) cooled to −78° C. To this mixture was slowly added dimethyl sulfoxide (303 μL, 4.26 mmol) and gas evolution occurred. The mixture was stirred at −78° C. for 30 min. After this time, a solution of bicyclo[2.2.1]hept-7-yl-methanol (180 mg, 1.43 mmol) in dichloromethane (5 mL) was added dropwise. The mixture was stirred at −78° C. for another 15 min and triethylamine (784 μL, 5.58 mmol) was added and the reaction was slowly warmed to 0° C. and stirred for 1 h. After this time, the mixture was quenched with a 1M aqueous sodium bisulfate solution (15 mL) and extracted with dichloromethane (3×10 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by AnaLogix IntelliFlash flash chromatography system (4 g column, 10% ethyl acetate/hexanes) afforded bicyclo[2.2.1]heptane-7-carbaldehyde (170 mg, 96%).

1. customIn a flask under argon was placed
2. stirringThe mixture was stirred at −78° C. for another 15 min
3. temperaturethe reaction was slowly warmed to 0° C.
4. stirringstirred for 1 h
5. customAfter this time, the mixture was quenched with a 1M aqueous sodium bisulfate solution (15 mL)
6. extractionextracted with dichloromethane (3×10 mL)
7. dry with materialThe combined organic layers were dried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customPurification by AnaLogix IntelliFlash flash chromatography system (4 g column, 10% ethyl acetate/hexanes)

ORD-Eintrag

ord-8eec720942394f658a4a6f005ac85813

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07741327B2