Water → methyl 1H-pyrrole-3-carboxylate

HRID 2090612Notes

Reaction equation

HRID 2090612 reaction equation
C[C:2]([CH3:5])([O-])C.[K+].C1(C)C=CC(S(C[N+:17]#[C-])(=O)=O)=CC=1.[C:20]([O:24][CH3:25])(=[O:23])[CH:21]=[CH2:22].O>O1CCCC1>[NH:17]1[CH:2]=[CH:5][C:21]([C:20]([O:24][CH3:25])=[O:23])=[CH:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 7294Methyl AcrylateHCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxide

Product 1

HCID 12361759methyl 1H-pyrrole-3-carboxylateYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of potassium tert-butoxide (17.9 g) in tetrahydrofuran (200 mL) was added dropwise a solution of p-toluenesulfonylmethyl isocyanide (25.2 g) and methyl acrylate (11.8 mL) in tetrahydrofuran (200 mL) over 30 min. The reaction mixture was stirred at room temperature for 1 hr, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1) to give the title compound as a white solid (yield 6.56 g, 41%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1)

Sources & evidence

ORD record
ord-60ab4885aa8e4f34a6ace3f24662b9e5
Source dataset
uspto-grants-2013_05
Patent number
US08436187B2

Reaction notes

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