Pyridine → HCID 86749865, compound

HRID 745031Notes

Reaction equation

HRID 745031 reaction equation
Cl[C:2]([O:4][CH:5]([Cl:7])[CH3:6])=[O:3].[CH3:8][O:9][CH2:10][CH2:11]O.N1C=CC=CC=1>C(Cl)(Cl)Cl>[C:2](=[O:3])([OH:9])[OH:4].[Cl:7][CH:5]([CH2:11][CH2:10][O:9][CH3:8])[CH3:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 80192-MethoxyethanolHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 86749865HCID 86749865, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-Chloroethyl chloroformate (28.6 g, 0.2 mol) and 2-methoxyethanol (13.7 g, 0.18 mol) were dissolved in chloroform (220 ml) at 0° C. Pyridine (15.8 g, 0.2 mol) was added dropwise during 45 minutes maintaining the temperature below 12° C. After stirring at room temperature for 2 hours the mixture was washed three times with 1 normal hydrochloric acid, once with a saturated sodium hydrogen carbonate solution and finally twice with water. The organic phase was dried with magnesium sulfate and the solvent was removed at reduced pressure. The residue was distilled in vacuo. Yield: 75%. 1H-NMR: delta=1.76 (CHCH3); 3.27 (OCH3); 3.55 (CH2OCH3); 4.27 (COOCH2); 6.51 (CH).

Workup

  1. temperaturemaintaining the temperature below 12° C
  2. washwas washed three times with 1 normal hydrochloric acid
  3. dry with materialThe organic phase was dried with magnesium sulfate
  4. customthe solvent was removed at reduced pressure
  5. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-c9d92dde582746c7a2154814d3880154
Source dataset
uspto-grants-1996_09
Patent number
US05559266

Reaction notes

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