Dimethyl Sulfoxide → 5-(Tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentanal

Temperature

-78 °C

To a solution of oxalyl chloride (0.97 mL, 11 mmol) (Aldrich) in dichloromethane (20 mL) at −78° C. was added the solution of dimethyl sulfoxide (1.6 mL, 22 mmol) in dichloromethane (5 mL) dropwise. After 5 mins, the solution of 5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentan-1-ol (2.5 g, 10 mmol) in dichloromethane (10 mL) was added dropwise. The reaction mixture was stirred at −78° C. for 15 min. Triethylamine (5 mL, 36 mmol) was added and the reaction mixture was slowly warmed up to room temperature and stirred at room temperature for 45 min. Then water was added. The organic layers were separated, and the aqueous layer was extracted with dichloromethane. The organic layers were combined, washed with 10% of HCl, saturated NaHCO3, brine, dried over MgSO4, and concentrated to give 5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentanal as a light yellow oil (Yield: 1.75 g, 71%).

1. temperaturethe reaction mixture was slowly warmed up to room temperature
2. stirringstirred at room temperature for 45 min
3. customThe organic layers were separated
4. extractionthe aqueous layer was extracted with dichloromethane
5. washwashed with 10% of HCl, saturated NaHCO3, brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated

ORD record

ord-5d07d86ca9384bafbc2850207f518ebd

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288431B2