Pyridine → alpha-Chlorobenzyl 2-(2-(2-methoxyethoxy)-ethoxy)-ethyl carbonate

HRID 1060788Notes

Reaction equation

HRID 1060788 reaction equation
Cl[C:2]([O:4][CH:5]([Cl:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH3:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][OH:23].N1C=CC=CC=1>ClCCl>[C:2](=[O:3])([O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH3:13])[O:4][CH:5]([Cl:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 8178Triethylene glycol monomethyl etherHCID 14320655Chloro(phenyl)methyl carbonochloridate

Product 1

HCID 18629469alpha-Chlorobenzyl 2-(2-(2-methoxyethoxy)-ethoxy)-ethyl carbonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

α-Chlorobenzyl chloroformate (1 g) was added to an ice-cold solution of triethyleneglycol monomethylether (0.7 ml) in dichloromethane (5 ml) followed by pyridine (0.43 ml) at such a rate that the temperature was kept below 10° C. After stirring overnight at room temperature the reaction mixture was washed twice with 0.5 M HCl followed by water and aqueous sodium bicarbonate. Drying over magnesium sulfate, filtration, evaporation in vacuo followed by chromatography on silica gel with hexane/ethyl acetate (1:1) as eluent gave the title compound as a colourless oil.

Workup

  1. customwas kept below 10° C
  2. washwas washed twice with 0.5 M HCl
  3. dry with materialDrying over magnesium sulfate, filtration, evaporation in vacuo

Sources & evidence

ORD record
ord-080662160f984ae08f0ed276d20d9278
Source dataset
uspto-grants-2003_02
Patent number
US06525077B2

Reaction notes

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