Dimethyl Sulfoxide → 2-Oxazolecarboxaldehyde, 5-(1,1-dimethylethyl)- (9CI)

To a stirred solution of oxalyl chloride (45 mL, 90 mmole) at −78 deg C. under argon was added dropwise dimethyl sulfoxide (8.80 mL, 124 mmole). The reaction mixture was stirred at −78 deg C. for 10 min., and was treated with a solution of 2-hydroxymethyl-5-t-butyloxazole (11.7 g, 75.1 mmole) in anhydrous methylene chloride (30 mL) over 20 min. The mixture was stirred at this temperature for 1 hour, then triethylamine was added slowly (31.0 mL, 222 mmole), during which the reaction mixture became a yellowish slurry. After stirring at −78 deg C. for 20 min, the reaction mixture was warmed to room temperature, added with methylene chloride (100 mL) and stirred for 1 hour. The solid was filtered off and washed with EtOAc. The filtrate was washed with 5% aqueous citric acid (100 mL) and brine (50 mL), dried over MgSO4. Concentration and column chromatography (silica gel, EtOAc/hexane 1:4) afforded 2-formyl-5-t-butyloxazole as a light yellow oil (10.1 g).

1. customat −78 deg C
2. stirringThe mixture was stirred at this temperature for 1 hour
3. stirringAfter stirring at −78 deg C
4. waitfor 20 min
5. stirringstirred for 1 hour
6. filtrationThe solid was filtered off
7. washwashed with EtOAc
8. washThe filtrate was washed with 5% aqueous citric acid (100 mL) and brine (50 mL)
9. dry with materialdried over MgSO4
10. concentrationConcentration and column chromatography (silica gel, EtOAc/hexane 1:4)

ORD record

ord-0458d115ed824ba6a04dd551ade56c9f

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06720347B2