Nitromethane → 2-Nitro-1-pyrazin-2-yl-ethanol

Reaction equation

[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH:7]=[O:8].C(N(CC)CC)C.[N+:16]([CH3:19])([O-:18])=[O:17]>>[N+:16]([CH2:19][CH:7]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]=1)[OH:8])([O-:18])=[O:17]

Participants

Reactant 3

HCID 6375Nitromethane

HCID 8471Triethylamine

HCID 11274980Pyrazine-2-carbaldehyde

Product 1

HCID 219281742-Nitro-1-pyrazin-2-yl-ethanolYield 93.3%

Procedure

To a round bottom flask was added 2-pyrazinecarboxaldehyde (770 mg, 7.12 mmol) in 10 mL of nitromethane, followed by the addition of triethylamine (721 mg, 7.12 mmol). The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo. The residue was loaded onto a flash chromatography column. The column was eluted with 0–5% MeOH/CH2Cl2. The product fractions were collected and concentrated to afford 1124 mg (93.3%) of 2-nitro-1-pyrazin-2-yl-ethanol. (TLC: Rf=0.2, 5% MeOH/CH2Cl2, UV).