Ethanol → Ethyl 3-(4-chlorophenyl)-1H-pyrrole-2-carboxylate

HRID 623723Notes

Reaction equation

HRID 623723 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/S(C2C=CC(C)=CC=2)(=O)=O)=[CH:6][CH:5]=1.[N+:22]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])#[C-:23].CCO>C1COCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[CH:23][NH:22][C:24]=2[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 533707Ethyl isocyanoacetateHCID 10979228(E)-1-Chloro-4-(2-tosylvinyl)benzene

Product 1

HCID 79327547Ethyl 3-(4-chlorophenyl)-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under N2, at 0° C. 60% NaH in mineral oil (3.11 g, 78 mmol) was added to a solution of (E)-1-chloro-4-(2-tosylvinyl)benzene (19 g, 64.9 mmol) in dry THF (300 mL). After 5 minutes ethyl 2-isocyanoacetate (7.76 mL, 71.4 mmol) was added and the reaction mixture stirred at room temperature. After 18 h EtOH (50 mL) was added and the solvents were evaporated under reduced pressure. The residue was partitioned between EtOAc (400 mL) and H2O (400 mL). The organic phase was washed with (100 mL), dried over Na2SO4, filtered and evaporated to dryness under reduced pressure. The crude product (16.55 g, “102%”) was used in the next step.

Workup

  1. customat 0° C
  2. customthe solvents were evaporated under reduced pressure
  3. customThe residue was partitioned between EtOAc (400 mL) and H2O (400 mL)
  4. washThe organic phase was washed with (100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-17ef1a45d9f04beface7019ce7fc451d
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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