Ethyl Acetate → 6-(Benzyloxy)-5-nitropicolinaldehyde

HRID 509397Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[C:11]([CH:18]=C)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[O:22]C(C)=O>CC(C)=O.O.CCCCCC.O=[Os](=O)(=O)=O>[CH2:1]([O:8][C:9]1[N:10]=[C:11]([CH:18]=[O:22])[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) stirred mixture of (2-(benzyloxy)-3-nitro-6-vinylpyridine (0.5 g, 0.0019 mol) in acetone:water (1:1, 5 mL), was added OsO4 (16.39 mg, 0.000064 mol, Aldrich) and NaIO4 (1.67 g, 0.0078 mol, Aldrich). The reaction mixture was stirred for 4 h at room temperature. After completion of the reaction (monitored by TLC, 10% EtOAc in hexane), the reaction mixture was quenched with water (10 mL) and extracted with EtOAc (5 mL×3). The organic layers were combined, dried over anhydrous sodium sulfate and purified by column chromatography, silica gel (60-120 mesh) using 5-7% EtOAc in petroleum ether as an eluent to afford the title compound. 1H NMR (400 MHz, CDCl3) δ: 10.00 (s, 1H), 8.38 (d, J=6 Hz, 1H), 7.69 (d, J=6 Hz, 1H), 7.54 (d, J=5.7 Hz, 2H), 7.41-7.37 (m, 3H), 5.69 (s, 2H).

Workup

stirringThe reaction mixture was stirred for 4 h at room temperature
customthe reaction mixture was quenched with water (10 mL)
extractionextracted with EtOAc (5 mL×3)
dry with materialdried over anhydrous sodium sulfate
custompurified by column chromatography, silica gel (60-120 mesh)

Sources & evidence

ORD record: ord-70dfa47629e942ab99deb6b86a0fa250
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096527B2

Reaction notes

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