Triacetoxyperiodinane → 4-Hydroxy-4-methyl-1-(4-nitrophenyl)pent-2-yn-1-one

To a room temperature solution of 4-methyl-1-(4-nitrophenyl) pent-2-yne-1,4-diol (2 g, 8.51 mmol, 1 eq) in dry DCM (100 mL) was added NaHCO3 (680 mg, 8.51 mmol, 1 eq) followed by Dess Martin Periodinane (9.2 g, 21.27 mmol, 2.5 eq). The reaction mixture was stirred at RT for 16 h. After completion of the reaction (as monitored by TLC), the reaction mixture was quenched with a saturated sodium bisulfite solution and extracted with DCM (2×100 mL). The combined organic layers were washed with water (100 mL) and brine (100 mL), dried over Na2SO4, filtered, and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography eluting with 20% EtOAc in hexanes to afford 4-hydroxy-4-methyl-1-(4-nitrophenyl)pent-2-yn-1-one (1.7 g, 86%) as an oil.

1. customAfter completion of the reaction (as monitored by TLC)
2. customthe reaction mixture was quenched with a saturated sodium bisulfite solution
3. extractionextracted with DCM (2×100 mL)
4. washThe combined organic layers were washed with water (100 mL) and brine (100 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto obtain the crude product
9. customThe crude material was purified via silica gel column chromatography
10. washeluting with 20% EtOAc in hexanes

ORD record

ord-0be7deec60f54e068a759f7531eb90d6

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466148B2