Benzyl chloroformate → HCID 20463131, compound

HRID 325934Notes

Reaction equation

HRID 325934 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([OH:14])=[O:13])=[N:10][CH:11]=1.[C:15](Cl)([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>N1C=CC=CC=1.C1(C)C=CC=CC=1>[C:15]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([OH:14])=[O:13])=[N:10][CH:11]=1)([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 20463145HCID 20463145, compound

Product 1

HCID 20463131HCID 20463131, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

3.92 g of 5-(4-hydroxybutyl)picolinic acid was dissolved in 20 ml of pyridine, and with stirring under ice cooling, a solution of 4.6 g of carbobenzyloxy chloride in 20 ml of toluene was added dropwise. Under ice cooling, the mixture was reacted for 2 hours. Then, the reaction mixture was poured into ice water, and extracted with toluene. The extract was washed successively with water, 1 N hydrochloric acid and then with water, and the toluene was distilled off to give 5.7 g of 5-(4-carbobenzyloxybutyl)picolinic acid.

Workup

  1. customUnder ice cooling, the mixture was reacted for 2 hours
  2. extractionextracted with toluene
  3. washThe extract was washed successively with water, 1 N hydrochloric acid
  4. distillationwith water, and the toluene was distilled off

Sources & evidence

ORD record
ord-f038b2a7d9624f8d8b30eb7529db5959
Source dataset
uspto-grants-1984_04
Patent number
US04443459

Reaction notes

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