Ethylene Glycol → HCID 21931671, compound

HRID 1244049Notes

Reaction equation

HRID 1244049 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH:12]=[O:13])=[N:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1.[CH2:14](O)[CH2:15][OH:16].O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:13]1[CH2:14][CH2:15][O:16][CH:12]1[C:4]1[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[C:6]([N+:9]([O-:11])=[O:10])[N:5]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 21931673HCID 21931673, compound

Product 1

HCID 21931671HCID 21931671, compoundYield 884.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 0.55 g (0.3 mmol) 3-methoxy-6-nitro-pyridine-2-carbaldehyde, 0.8 ml (15 mmol) of ethylene glycol, and 10 mg (catalytic amount) of p-toluene sulfonic acid was refluxed in 50 ml of toluene using a Dean-Stark trap to trap water. After 90 minutes, the reaction mixture was cooled to room temperature and the solvent evaporated. The residue was chromatographed on silica using 5:1 (chloroform/ethyl acetate) as the elutant. Appropriate fractions were combined and evaporated to yield 0.6 g of 2-[1,3]dioxolan-2-yl-3-methoxy-6-nitro-pyridine as an oil. TLC: Rf=0.9 (1:1 chloroform/ethyl acetate). 1H NMR (CDCl3) δ 8.25 (d, 1H), 7.40 (d, 1H), 6.30 (s, 1H), 4.30 (m, 2H), 4.10 (m, 2H), 4.0 (s, 3H). Mass Spectrum: m/e=227.2 (p+1).

Workup

  1. customthe solvent evaporated
  2. customThe residue was chromatographed on silica using 5:1 (chloroform/ethyl acetate) as the elutant
  3. customevaporated

Sources & evidence

ORD record
ord-453be4af762b49f6aa028a577e4fc942
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

Loading…