Dimethyl Sulfoxide → 4-((Tert-butyldimethylsilyl)oxy)butanal

Temperature

-78 °C

To CH2Cl2 (150 mL) at −78° C. were added oxalyl chloride (6.83 g, 53.8 mmol) and dry DMSO (8.41 g, 108 mmol), dropwise. After 5 min, 4-(tert-butyldimethylsilyloxy)butan-1-ol (10 g, 48.9 mmol) in CH2Cl2 (5 mL) was added dropwise. The mixture was stirred for an additional 30 min at −78° C., and Et3N (24.8 g, 245 mmol) was added. The mixture was then allowed to warm to room temperature over 30 min. After stirring for 3 hrs, 100 mL of water was added. The phases were separated, and the aqueous phase was extracted three times with 100 mL of diethyl ether. The combined organic phases were washed successively with 50 mL of aqueous 1% HCl, 50 mL of water, 50 mL of aqueous 5% NaHCO3 and 50 mL of saturated aqueous NaCl. The organic layer was dried over MgSO4, and the solvent was removed under reduced pressure, to provide the title compound.

1. temperatureto warm to room temperature over 30 min
2. stirringAfter stirring for 3 hrs
3. customThe phases were separated
4. extractionthe aqueous phase was extracted three times with 100 mL of diethyl ether
5. washThe combined organic phases were washed successively with 50 mL of aqueous 1% HCl, 50 mL of water, 50 mL of aqueous 5% NaHCO3 and 50 mL of saturated aqueous NaCl
6. dry with materialThe organic layer was dried over MgSO4
7. customthe solvent was removed under reduced pressure

ORD record

ord-0a3996bc272c45f49b719c2382a62d3a

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08835475B2