Ethyl chloroformate → HCID 14371280, compound

HRID 476890Notes

Reaction equation

HRID 476890 reaction equation
[CH2:1]([O:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[CH:6]1)[CH3:2].C([Li])CCC.Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C1COCC1.CCCCCC>[CH2:1]([O:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:2]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 19837065HCID 19837065, compoundHCID 178418339Butyllithium

Product 1

HCID 14371280HCID 14371280, compoundYield 35.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-60 °C

Procedure

1-Ethoxymethylbenzimidazole (1.76 g) was dissolved in dry THF (40 ml) in a dry argon atmosphere, cooled to -60° C., and a solution of n-butyl lithium (1.58M) in hexane (9 ml) was added dropwise with stirring and allowed to react for 1 hr. After ethyl chloroformate (1.62 g) was added dropwise, the mixture was slowly returned to room temperature and allowed to react overnight. THF was distilled off, the residue was dissolved in ethyl acetate, washed with water, dried over anhydrous Na2SO4, and the solvent was distilled off. Purification of the residue by column chromatography on silica gel gave the title compound (0.89 g) as an oily product.

Workup

  1. customto react for 1 hr
  2. customwas slowly returned to room temperature
  3. customto react overnight
  4. distillationTHF was distilled off
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washwashed with water
  7. dry with materialdried over anhydrous Na2SO4
  8. distillationthe solvent was distilled off
  9. customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-6a19b9a7847b4709ae0124998d8129b5
Source dataset
uspto-grants-1989_12
Patent number
US04886803

Reaction notes

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