Tert-Butyl hypochlorite → HCID 12897088, compound

HRID 894070Notes

Reaction equation

HRID 894070 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[CH:2]1.C(O[Cl:15])(C)(C)C>C(Cl)Cl>[Cl:15][C:5]1[NH:1][CH:2]=[C:3]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=1

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 12361759methyl 1H-pyrrole-3-carboxylate

Product 1

HCID 12897088HCID 12897088, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl pyrrole-3-carboxylate (2.5 g., 20 mmoles) was dissolved in 50 ml. of methylene chloride. The solution, stirred under nitrogen, was cooled in an ice-water bath while t-butylhypochlorite (1.95 g., 18 mmoles) in 25 ml. of methylene chloride was added dropwise. The reaction was stirred for 1 hour at room temperature, filtered and evaporated to an oil. The oil was chromatographed (100 g. silica gel with ethyl acetate-1/hexane-7 as eluant). The column elution was monitored by thin layer chromatography (silica gel plates with chloroform-8/ethyl acetate-2 as eluant). Cuts containing pure product (Rf 0.4) were combined and evaporated to yield crystalline methyl 5-chloropyrrole-3-carboxylate (900 mg., m.p. 92°.95° C., m/e 159/161).

Workup

  1. stirringThe reaction was stirred for 1 hour at room temperature
  2. filtrationfiltered
  3. customevaporated to an oil
  4. customThe oil was chromatographed (100 g. silica gel with ethyl acetate-1/hexane-7 as eluant)
  5. washThe column elution
  6. additionCuts containing pure product (Rf 0.4)
  7. customevaporated

Sources & evidence

ORD record
ord-d18908914be04acfa70858b9cb3e2d2d
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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