Water → Ethyl 4-(2-nitrophenyl)-1H-pyrrole-3-carboxylate

HRID 2360585Notes

Reaction equation

HRID 2360585 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])([O-:3])=[O:2].C1(C)C=CC(S([CH2:26][N:27]=[C:28]=O)(=O)=O)=CC=1.[H-].[Na+].O>CS(C)=O.C(OCC)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:26][NH:27][CH:28]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 117890781-Isocyanatomethanesulfonyl-4-methylbenzeneHCID 13204958Ethyl 3-(2-nitrophenyl)propanoate

Product 1

HCID 12065081Ethyl 4-(2-nitrophenyl)-1H-pyrrole-3-carboxylateYield 41%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of ethyl 3-(2-nitrophenyl)propanoate (120 mmol; 26.6 g) and 4-toluenesulfonylmethyl isocyanate (TosMIC) (130 mmol; 25.4 g) in a mixture of dimethyl sulfoxide and anhydrous ethyl ether (150 and 300 ml) was added dropwise to a suspension of 60% sodium hydride in paraffin (260 mmol; 10.4 g) in anhydrous ethyl ether (300 ml), under a stream of argon. After the addition, the mixture was stirred at room temperature for 25 minutes, water (500 ml) was then added and the resulting solution was extracted with ethyl acetate (3×600 ml). The combined organic phases were washed with saturated NaCl solution (3×300 ml), dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product obtained was purified on a column of alumina (eluting with a 1/1 chloroform/ethyl acetate mixture) to give 12.8 g (41%) of final product having the following characteristics:

Workup

  1. additionAfter the addition
  2. extractionthe resulting solution was extracted with ethyl acetate (3×600 ml)
  3. washThe combined organic phases were washed with saturated NaCl solution (3×300 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe crude product obtained
  7. customwas purified on a column of alumina (
  8. washeluting with a 1/1 chloroform/ethyl acetate mixture)

Sources & evidence

ORD record
ord-ec93581952b04faaa323fb1137edccdc
Source dataset
uspto-grants-2014_04
Patent number
US08686147B2

Reaction notes

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