Water → HCID 14873720, compound

HRID 621806Notes

Reaction equation

HRID 621806 reaction equation
[Br:1][C:2]1[C:3]([O:12][CH:13]([CH3:15])[CH3:14])=[C:4]([C:8]([O:10]C)=[O:9])[NH:5][C:6]=1[Br:7].CC(C)([O-])C.[K+].O>CS(C)=O>[Br:1][C:2]1[C:3]([O:12][CH:13]([CH3:15])[CH3:14])=[C:4]([C:8]([OH:10])=[O:9])[NH:5][C:6]=1[Br:7]

Participants

5

Reactant 3

HCID 962WaterHCID 14154273HCID 14154273, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14873720HCID 14873720, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Methyl 4,5-dibromo-3-(1-methylethoxy)-1H-pyrrole-2-carboxylate (1.5 g, 0.004 moles) is stirred under nitrogen in DMSO (100 mL) at room temperature. Potassium tert-butoxide (2.5 g, 0.022 moles) is added. After 12 hours the mixture is stirred into water (600 mL) and extracted with ether twice. The ether extracts are discarded, and the aqueous phase is acidified with H3PO4, then extracted with CH2Cl2 (3x). The combined extracts are washed with brine and dried over MgSO4. Removal of the solvent under reduced pressure left the product as a clear oil (1.4 g), sufficiently pure for further use.

Workup

  1. extractionextracted with ether twice
  2. extractionextracted with CH2Cl2 (3x)
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over MgSO4
  5. customRemoval of the solvent under reduced pressure
  6. waitleft the product as a clear oil (1.4 g)

Sources & evidence

ORD record
ord-00d5edc308dd4bc6ae87ff78b5b20e31
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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