Dimethyl Sulfoxide → HCID 54105440, compound

Temperature

-78 °C

A solution of dimethylsulfoxide (2,578 ml. 36.3 mmol) in methylene chloride (3 ml) was added dropwise at -78° C. to a stirred solution of oxalyl chloride (1.585 ml, 18.2 mmol) over 5 minutes and stirred at -78° C. for 10 minutes. A solution of (R)-2,3,3-trimethyl-1,2-butanediol in methylene chloride (25 ml) was added dropwise and stirred for 15 minutes at -78° C. Triethylamine (11.51 ml, 82.6 mmol) was added and the reaction was allowed to come to room temperature. The mixture was diluted with additional methylene chloride, washed with 10% sulfuric acid, the combined aqueous phase was extracted with methylene chloride, and the combined organic layer was washed with saturated sodium bicarbonate, dried (magnesium sulfate), and concentrated by distillation at atmospheric pressure to afford 2.15 g of (R)-2,3,3-trimethyl-2-hydroxybutanal as a pale gummy solid.

1. stirringstirred for 15 minutes at -78° C
2. customto come to room temperature
3. washwashed with 10% sulfuric acid
4. extractionthe combined aqueous phase was extracted with methylene chloride
5. washthe combined organic layer was washed with saturated sodium bicarbonate
6. dry with materialdried (magnesium sulfate)
7. concentrationconcentrated by distillation at atmospheric pressure

ORD record

ord-45527cfe074a4fdf8a48ae0a83b0e501

Source dataset

uspto-grants-1996_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05492910