Dimethyl Sulfoxide → 2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde

Temperature

-60 °C

A solution of anhydrous DMSO (3.41 mL, 48 mmol) in CH2Cl2 (5 mL) was added dropwise to a stirred solution of oxalyl chloride (1.92 mL, 22 mmol) in CH2Cl2 (50 mL) at −60° C. To this mixture was added a solution of (2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol (2.48 mL, 20 mmol) in CH2Cl2 (10 mL). The resulting mixture was stirred for 15 min at −60° C. TEA (13.9 mL, 100 mmol) was added dropwise. The reaction mixture was then warmed to room temperature. Water (50 mL) and CH2Cl2 (50 mL) were added. The organic layer was separated and washed with water (25 mL). The aqueous layer was extracted with CH2Cl2 (3×50 mL). The organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to afford the crude 2,2-dimethyl-1,3-dioxolane-4-carbaldehyde that was used directly without further purification.

1. temperatureThe reaction mixture was then warmed to room temperature
2. customThe organic layer was separated
3. washwashed with water (25 mL)
4. extractionThe aqueous layer was extracted with CH2Cl2 (3×50 mL)
5. dry with materialThe organic layers were dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure

ORD record

ord-cb8ab75ac5b34eb38eb55a4c4112ef1c

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242964B2