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

Temperature

-60 °C

To a solution of oxalyl chloride (31.7 ml) in dry dichloromethane (100 ml) cooled to -60° C., was added a solution of dimethylsulfoxide (9.8 ml) in dichloromethane (30 ml) followed by a slurry of 3-(1-decyl)-5-isoxazolemethanol (13.8 g) in dry dichloromethane (100 ml). The reaction mixture was stirred at -60° C. for 0.5 hr, quenched with triethylamine (40 ml), and allowed to warm to ambient temperature. The solution was poured into water (300 ml) and extracted with dichloromethane. The organic phases were washed with dilute citric acid, dried, and evaporated. The residue was flash chromatographed (silica, 50:1-dichloromethane:methanol). The appropriate fraction were collected and evaporated. The residue was recrystallized from ether-hexane to give 11.2 g (82%) of product, mp 46°-48° C.

1. customquenched with triethylamine (40 ml)
2. temperatureto warm to ambient temperature
3. additionThe solution was poured into water (300 ml)
4. extractionextracted with dichloromethane
5. washThe organic phases were washed with dilute citric acid
6. customdried
7. customevaporated
8. customchromatographed (silica, 50:1-dichloromethane:methanol)
9. customThe appropriate fraction were collected
10. customevaporated
11. customThe residue was recrystallized from ether-hexane

ORD record

ord-fe3df45ec8774a759909b8f77c8ecf59

Source dataset

uspto-grants-1996_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05550247