Triacetoxyperiodinane → Acetamide, 2,2,2-trifluoro-N-(4-oxobutyl)-

Temperature

0 °C

N-(4-hydroxybutyl)trifluoroacetamide (1.65 g; 8.9 mmol) was dissolved in anhydrous DCM (9 mL) and cooled to 0° C. A solution of Dess-Martin periodinane (15% in DCM; 30 mL; 14.0 mmol) was added to the cooled solution and stirred first at 0° C. for 10 min and then at room temperature for 2.5 h. The reaction was quenched with 1:1 10% sodium thiosulfate and saturated NaHCO3 and the biphasic mixture vigorously stirred for 30 min. The layers were separated and the aqueous layer extracted with DCM. The combined organic layers were dried over MgSO4, filtrated and evaporated. The residue was purified by column chromatography (Hex:EtOAc 2:1+1% MeOH) providing N-(4-oxobutyl)trifluoroacetamide in a yield of 1.15 mg (71%).

1. waitat room temperature for 2.5 h
2. customThe reaction was quenched with 1:1 10% sodium thiosulfate and saturated NaHCO3
3. stirringthe biphasic mixture vigorously stirred for 30 min
4. customThe layers were separated
5. extractionthe aqueous layer extracted with DCM
6. dry with materialThe combined organic layers were dried over MgSO4
7. filtrationfiltrated
8. customevaporated
9. customThe residue was purified by column chromatography (Hex:EtOAc 2:1+1% MeOH)

ORD record

ord-157ff8a18b044c3085bfad4150c0f97f

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422232B2