Pyridine → 1-Chloroethyl thenyl carbonate

HRID 745029Notes

Reaction equation

HRID 745029 reaction equation
Cl[C:2]([O:4][CH:5]([Cl:7])[CH3:6])=[O:3].[OH:8][CH2:9][C:10]1[S:11][CH:12]=[CH:13][CH:14]=1.N1C=CC=CC=1>C(Cl)(Cl)Cl>[C:2](=[O:3])([O:8][CH2:9][C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[O:4][CH:5]([Cl:7])[CH3:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 694672-ThiophenemethanolHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 199378721-Chloroethyl thenyl carbonate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-Chloroethyl chloroformate (28.6 g, 0.2 mol) and 2-hydroxymethyl-thiophene (20.6 g, 0.18 mol) were dissolved in chloroform (220 ml) at 0° C. Pyridine (15.8 g, 0.2 mol) was added dropwise during 35 minutes maintaining the temperature below 10° C. After stirring at room temperature for 24 hours the precipitate was filtered off. The organic phase was washed three times with 1 normal hydrochloric acid, once with a saturated sodium hydrogen carbonate solution and finally twice with water. The organic solution was dried with magnesium sulfate and the solvent was removed at reduced pressure. The residue was distilled in vacuo. Yield: 36.5 g. 1H-NMR (DMSO-d6): delta=1.76 (CH3); 5.41 (CH2); 6.53 (CHCH3); 7.04, 7.25; 7.59 ppm (thiophene).

Workup

  1. temperaturemaintaining the temperature below 10° C
  2. filtrationwas filtered off
  3. washThe organic phase was washed three times with 1 normal hydrochloric acid
  4. dry with materialThe organic solution was dried with magnesium sulfate
  5. customthe solvent was removed at reduced pressure
  6. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-c72f3e13247e4bb4ab5245e64115b173
Source dataset
uspto-grants-1996_09
Patent number
US05559266

Reaction notes

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