Methane, dichloromethoxy- → Ethyl 4-formyl-1H-pyrrole-2-carboxylate

HRID 1258056Notes

Reaction equation

HRID 1258056 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH2:9][CH3:10])=[O:7].[Al+3].[Cl-].[Cl-].[Cl-].[CH3:15][O:16]C(Cl)Cl>ClCCCl.[N+](C)([O-])=O>[CH:15]([C:4]1[CH:3]=[C:2]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[NH:1][CH:5]=1)=[O:16]

Participants

5

Reactant 3

HCID 21004Methane, dichloromethoxy-HCID 255670Ethyl 1H-pyrrole-2-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 321486Ethyl 4-formyl-1H-pyrrole-2-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 86610042HCID 86610042, compoundSolvent

Procedure

To a mixture of ethyl pyrrole-2-carboxylate (8.1 g, 58.3 mmol) and AlCl3 (15.5 g, 2 equiv) in 1,2-dichloroethane-nitromethane (1:1, 120 ml) was added α,α,-dichloromethyl methyl ether (6.4 mL, 2 equiv) dropwise at −20° C. Stirring was continued for 1 h at −20° C. and the reaction mixture was stored at −20° C. overnight. It was then poured into ice. Organic layer was separated and aqueous layer was extracted with DCM. The combined organic layers were washed with water, aqueous NH4OH and water and dried over Na2SO4. Evaporation of solvent afforded ethyl 4-formylpyrrole-2-carboxylate as a solid (8.8 g, 90%). 1H-NMR(CDCl3): δ 10.40 (1H, s), 8.95 (1H, s), 7.60 (1H, dd), 7.33 (1H, dd), 4.36 (2H, q), 1.39 (3H, t).

Workup

  1. waitthe reaction mixture was stored at −20° C. overnight
  2. additionIt was then poured into ice
  3. customOrganic layer was separated
  4. extractionaqueous layer was extracted with DCM
  5. washThe combined organic layers were washed with water, aqueous NH4OH and water
  6. dry with materialdried over Na2SO4
  7. customEvaporation of solvent

Sources & evidence

ORD record
ord-6962565eae3c4b9c8c3b9051255dfabe
Source dataset
uspto-grants-2013_06
Patent number
US08466143B2

Reaction notes

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