Methyl Glycolate → HCID 18619139, compound

HRID 1836445Notes

Reaction equation

HRID 1836445 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]([O:15][CH3:16])(=[O:14])[CH2:12][OH:13].CC(C)([O-])C.[K+]>C1COCC1>[CH3:16][O:15][C:11](=[O:14])[CH2:12][O:13][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 66774Methyl GlycolateHCID 783082-Chloro-5-nitropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 18619139HCID 18619139, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-5-nitropyridine (1.0 g, 6.3 mmol) and methyl glycolate (0.67 mL, 8.2 mmol) in THF (10 mL) was added potassium tert-butoxide (0.92 g, 8.2 mmol) in one portion. After 1 h the reaction was poured onto ice, the solids isolated by filtration and washed with water. Purification on silica gel by column chromatography using 20% ethyl acetate in hexanes gave 0.23 g (18%) of the titled product as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 9.02 (m, 1H), 7.15 (m, 1H), 5.06 (s, 2H), 3.65 (s, 3H).

Workup

  1. additionAfter 1 h the reaction was poured onto ice
  2. customthe solids isolated by filtration
  3. washwashed with water
  4. customPurification on silica gel by column chromatography

Sources & evidence

ORD record
ord-0920eba5c84d4e63b9813e0ce51497b7
Source dataset
uspto-grants-2004_08
Patent number
US06777432B1

Reaction notes

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