Triacetoxyperiodinane → 1-isopropyl-1H-pyrazole-3-carbaldehyde

To the (1-Isopropyl-1H-pyrazol-3-yl)-methanol from the above reaction was added CH2Cl2 (1.10 L). Dess-Martin periodinane (144 g, 339 mmol) was then added portionwise. The reaction was stirred at room temperature. After 1 h, more Dess-Martin periodinane (16.0 g, 37.7 mmol) was added. The reaction was allowed to stir for 11 h, at which point starting material was no longer detectable by LCMS. The reaction mixture was filtered through celite. The filtrate was then washed with sat. aq. NaHCO3 (3×300 mL) followed by brine (150 mL). The organic was dried over MgSO4, filtered, and concentrated. This crude product was then dry loaded onto the ISCO and eluted with CH2Cl2 to give the purified product (18.8 g, 61%) as a pale yellow oil.

1. stirringto stir for 11 h, at which point
2. filtrationThe reaction mixture was filtered through celite
3. washThe filtrate was then washed with sat. aq. NaHCO3 (3×300 mL)
4. dry with materialThe organic was dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. dry with materialThis crude product was then dry
8. washeluted with CH2Cl2

ORD record

ord-06f312308a7c4321bac5c3d33dcab8d1

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08853202B2