Nitromethane → HCID 67360344, compound

HRID 530614Notes

Reaction equation

HRID 530614 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][N:4]=1.C(N(CC)CC)C.[N+:20]([CH3:23])([O-:22])=[O:21]>>[N+:20]([CH2:23][CH:7]([C:6]1[CH:5]=[N:4][C:3]([C:2]([F:1])([F:11])[F:12])=[CH:10][CH:9]=1)[OH:8])([O-:22])=[O:21]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 8471TriethylamineHCID 27777626-(Trifluoromethyl)pyridine-3-carboxaldehyde

Product 1

HCID 67360344HCID 67360344, compound

Procedure

In a 100 mL round-bottomed flask, 6-(trifluoromethyl)nicotinaldehyde (2.61 g, 14.9 mmol) was combined with nitromethane (20 ml) to give a light yellow solution. triethylamine (1.51 g, 2.08 ml, 14.9 mmol) was added. The reaction mixture was stirred at room temperature for 1.5 h and concentrated in vacuo. The resultant residue was purified by flash chromatography (silica gel, 80 g, 0.2% to 1.2% MeOH in dichloromethane gradient) to afford 2-nitro-1-(6-(trifluoromethyl)pyridin-3-yl)ethanol (2.4 g) as an off-white solid.

Workup

  1. customto give a light yellow solution
  2. concentrationconcentrated in vacuo
  3. customThe resultant residue was purified by flash chromatography (silica gel, 80 g, 0.2% to 1.2% MeOH in dichloromethane gradient)

Sources & evidence

ORD record
ord-8f65700086764c0c8a7652e7afb66cc1
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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