Diisobutylaluminum hydride → 2-(4-Nitrophenyl)prop-2-en-1-ol

Temperature

0 °C

To a stirred solution of methyl 2-(4-nitrophenyl)acrylate (4.0 g, 19.323 mmol, 1.0 eq) in ether (40 mL) was added DIBALH (20% solution in toluene) (40 mL, 57.97 mmol, 3.0 eq) at −78° C., then the mixture was allowed to warm to 0° C. over a period of 2 h, then the mixture was quenched with water (1.0 mL), NaOH solution (15%) (3 mL), extracted with ether (20 mL×2), washed with water (20 mL), brine (20 mL), dried (MgSO4) and the solvent evaporated. The resulting residue was purified by CC using EtOAc/PE (3:7) as eluent to get 2-(4-nitrophenyl)prop-2-en-1-ol (1.5 g, 43%, oil); TLC system: EtOAc/PE (1:1), Rf: 0.4).

1. customthe mixture was quenched with water (1.0 mL), NaOH solution (15%) (3 mL)
2. extractionextracted with ether (20 mL×2)
3. washwashed with water (20 mL), brine (20 mL)
4. dry with materialdried (MgSO4)
5. customthe solvent evaporated
6. customThe resulting residue was purified by CC

ORD record

ord-a6772811761d4643b94ab10f14703773

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946204B2