Dimethyl Sulfoxide → 3-(1-Dodecyl)-5-isoxazolecarboxaldehyde

Temperature

-60 °C

A solution of oxalyl chloride (28.8 ml) in dry dichloromethane (100 ml) was cooled to -60° C. and a solution of dimethylsulfoxide (8.9 ml) in dichloromethane (30 ml) was added, followed by a slurry of 3-(1-dodecyl)-5-isoxazolemethanol (14.0 g) in dry dichloromethane (200 ml). The mixture was stirred at -60° C. for 1 hr, quenched with triethylamine (87 ml) and allowed to warm to room temperature. The solution was poured into water (300 ml) and extracted with dichloromethane. The organic phases were washed with dilute citric acid solution, dried, filtered, and the filtrate was evaporated. The residue was passed through a short pad of silica gel using dichloromethane as the eluent. The solution was evaporated and the residue was recrystallized from ether-hexane to give 11.5 g (78%) of product, mp 53°-54° C.

1. customquenched with triethylamine (87 ml)
2. temperatureto warm to room temperature
3. additionThe solution was poured into water (300 ml)
4. extractionextracted with dichloromethane
5. washThe organic phases were washed with dilute citric acid solution
6. customdried
7. filtrationfiltered
8. customthe filtrate was evaporated
9. customThe solution was evaporated
10. customthe residue was recrystallized from ether-hexane

ORD record

ord-19c7d3390ef44e248e93779308b9e491

Source dataset

uspto-grants-1996_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05574164