3-Nitrophenol → HCID 59464179, compound

DEAD (1.97 mL, 10.8 mmol) was added dropwise to a stirred mixture of 3-nitrophenol (2.50 g, 18 mmol), (2S)-1-methoxypropan-2-ol (648 mg, 7.2 mmol) and triphenylphosphine (2.84 g, 10.8 mmol) in DCM (10 ml). The reaction mixture was stirred for 16 h then treated with saturated aqueous sodium hydrogen carbonate solution. The resultant mixture was partitioned and the organics were washed with 1M NaOH, dried and concentrated by evaporation. The residue was triturated with 1:1 EtOAC/hexanes. and filtered. The filtrate was concentrated by evaporation and the residue was purified by chromatography eluting with 25% EtOAc/hexane to give the title compound (1 g) as an oil; 1H NMR (400 MHz, DMSO) δ1.24 (d, 3H), 3.24 (s, 3H), 3.44-3.60 (m, 2H), 4.71-4.89 (m, 1H), 7.38-7.48 (m, 1H), 7.57 (t, 1H), 7.70-7.76 (m, 1H), 7.76-7.86 (m, 1H).

1. customThe resultant mixture was partitioned
2. washthe organics were washed with 1M NaOH
3. customdried
4. concentrationconcentrated by evaporation
5. customThe residue was triturated with 1:1 EtOAC/hexanes
6. filtrationand filtered
7. concentrationThe filtrate was concentrated by evaporation
8. customthe residue was purified by chromatography
9. washeluting with 25% EtOAc/hexane

ORD record

ord-a78fef8468f34f8eab35af4a6da305b7

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07795283B2