Triethylamine → 28523-30-0

Temperature

-78 °C

Oxalyl chloride (7.8 g, 61.42 mmol) in methylene chloride (60 mL) at −78° C. was treated with dimethylsufoxide (8.4 g, 107.5 mmol). After stirring at −78° C. for 10 minutes, the mixture was treated with 2-cyclohexyl-2-methylpropanol (4.8 g, 36.86 mmol) in 15 ml of methylene chloride. The mixture was allowed to stir at −78° C. for 30 minutes and then treated with triethylamine (15.54 g, 153.6 mmol). The reaction mixture was stirred for 10 minutes and then stirred an additional 5 minutes at 0° C. The mixture was quenched with saturated aqueous ammonium (10 mL) chloride and extracted with diethyl ether (2×50 mL). The organic layer was washed with brine (15 mL), dried over anhydrous sodium sulfate and concentrated under vacuo. The crude product was redissolved in diethyl ether and the resulting precipitate was filtered through a pad of Celite. The solution was concentrated under reduced pressure to provide 4.5 g of 2-cyclohexyl-2-methylpropanal as an oil.

1. stirringto stir at −78° C. for 30 minutes
2. stirringThe reaction mixture was stirred for 10 minutes
3. stirringstirred an additional 5 minutes at 0° C
4. customThe mixture was quenched with saturated aqueous ammonium (10 mL) chloride
5. extractionextracted with diethyl ether (2×50 mL)
6. washThe organic layer was washed with brine (15 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under vacuo
9. dissolutionThe crude product was redissolved in diethyl ether
10. filtrationthe resulting precipitate was filtered through a pad of Celite
11. concentrationThe solution was concentrated under reduced pressure

ORD record

ord-e943043982404236885c218e75e1ce48

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06645968B2