Pyridine → Methyl {[(4-nitrophenoxy)carbonyl]oxy}acetate

HRID 2176003Notes

Reaction equation

HRID 2176003 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][OH:3].N1C=CC=CC=1.Cl[C:14]([O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)=[O:15]>C(Cl)Cl>[N+:23]([C:20]1[CH:21]=[CH:22][C:17]([O:16][C:14]([O:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])=[O:15])=[CH:18][CH:19]=1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 66774Methyl GlycolateHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 90377585Methyl {[(4-nitrophenoxy)carbonyl]oxy}acetateYield 17.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 640 mg of methyl glycolate, 0.60 mL of pyridine, and 10 mL of methylene chloride was added to 10 mL of a methylene chloride solution including 1.44 g of 4-nitrophenyl chloroformate at room temperature, followed by stirring for 2 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and diethyl ether and water were added to the residue and an organic layer was separated. The organic layer was sequentially washed with water and saturated brine and dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel column chromatography (using chloroform only), thereby obtaining 320 mg of methyl {[(4-nitrophenoxy)carbonyl]oxy}acetate.

Workup

  1. customat room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and diethyl ether and water
  3. additionwere added to the residue
  4. customan organic layer was separated
  5. washThe organic layer was sequentially washed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationfollowed by concentration under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-1ca31ed2a81144edad6e429a4a6edf65
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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