Methyl Acrylate → methyl 1H-pyrrole-3-carboxylate

HRID 2275406Notes

Reaction equation

HRID 2275406 reaction equation
C[C:2]([CH3:5])([O-])C.[K+].[C:7]([O:11][CH3:12])(=[O:10])[CH:8]=[CH2:9].C1(C)C(S(C[N+:23]#[C-])(=O)=O)=CC=CC=1>C1COCC1>[NH:23]1[CH:2]=[CH:5][C:8]([C:7]([O:11][CH3:12])=[O:10])=[CH:9]1

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 23665647Potassium tert-butoxideHCID 53627694Toluenesulfonylmethyl isocyanide

Product 1

HCID 12361759methyl 1H-pyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of potassium-tert-butoxide (105 g) in THF (1.2 L) was added dropwise a solution of methyl acrylate (66 g) and toluenesulfonylmethyl isocyanide (150 g) in THF (300 ml). The resulting mixture was stirred at room temperature for 2 h. The reaction was quenched with water and extracted with ethyl acetate. The organic phase was dried (MgSO4), filtered and concentrated. The crude product was purified by chromatography on silica gel (Petrol:ethyl acetate=5:1) to give the desired compound.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by chromatography on silica gel (Petrol:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-baf4af12825348ff85d8279c36e75f97
Source dataset
uspto-grants-2015_09
Patent number
US09127007B2

Reaction notes

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