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

HRID 554183Notes

Reaction equation

HRID 554183 reaction equation
C1(C)C=CC(S(C[N+:11]#[C-])(=O)=O)=CC=1.[C:14]([O:18][CH3:19])(=[O:17])[CH:15]=[CH2:16].C[C:21]([CH3:24])([O-])C.[K+]>O1CCCC1>[NH:11]1[CH:21]=[CH:24][C:15]([C:14]([O:18][CH3:19])=[O:17])=[CH:16]1

Participants

5

Reactant 3

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

Product 1

HCID 12361759methyl 1H-pyrrole-3-carboxylateYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution (250 mL) of p-toluenesulfonylmethyl isocyanide (15.0 g) and methyl acrylate (6.92 mL) in tetrahydrofuran was added dropwise to a suspension (100 mL) of potassium tert-butoxide in tetrahydrofuran over 30 min. The reaction mixture was stirred at room temperature for 1 hr, and filtered through a glass filter filled with silica gel (diameter 8 cm, height 4 cm), and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→2:1) to give the title compound as a pale-yellow solid (yield 4.69 g, 49%).

Workup

  1. filtrationfiltered through a glass
  2. filtrationfilter
  3. additionfilled with silica gel (diameter 8 cm, height 4 cm)
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→2:1)

Sources & evidence

ORD record
ord-b403ed83b5e84bf69c953dfae5ec4049
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

Loading…