Tosylmethyl isocyanide → Methyl 4-methyl-1H-pyrrole-3-carboxylate

HRID 1877280Notes

Reaction equation

HRID 1877280 reaction equation
CC(C)([O-])C.[K+].C1(C)C=CC(S([CH2:16][N+:17]#[C-:18])(=O)=O)=CC=1.[C:20]([O:25][CH3:26])(=[O:24])/[CH:21]=[CH:22]/[CH3:23]>O1CCCC1>[CH3:23][C:22]1[C:21]([C:20]([O:25][CH3:26])=[O:24])=[CH:16][NH:17][CH:18]=1

Participants

5

Reactant 3

HCID 161915Tosylmethyl isocyanideHCID 638132Methyl CrotonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 15274278Methyl 4-methyl-1H-pyrrole-3-carboxylateYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (100 mL) of potassium t-butoxide (23.0 g) in tetrahydrofuran was added dropwise a solution (50 mL) of p-toluenesulfonylmethyl isocyanide (25.0 g) and methyl crotonate (12.3 mL) in tetrahydrofuran with stirring under ice-cooling. After the completion of the dropwise addition, the ice bath was removed, and the reaction mixture was stirred at room temperature for 1 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:4, volume ratio) to give the title compound (7.6 g, 42%) as an oil.

Workup

  1. temperaturecooling
  2. additionAfter the completion of the dropwise addition
  3. customthe ice bath was removed
  4. stirringthe reaction mixture was stirred at room temperature for 1 hr
  5. filtrationThe reaction mixture was filtered through celite
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=1:4, volume ratio)

Sources & evidence

ORD record
ord-d12043ad12c1453b9d23546492cc4151
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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