Triethylamine → HCID 59478027, compound

HRID 1516606Notes

Reaction equation

HRID 1516606 reaction equation
C([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14]([CH2:16][OH:17])[C:13]([C:18]#[N:19])=[CH:12]2)=[CH:7][CH:6]=1)C.[CH2:21](N(CC)CC)[CH3:22].CS(Cl)(=O)=O>O1CCCC1>[C:18]([C:13]1[C:14]([CH2:16][O:17][CH2:21][CH3:22])=[CH:15][N:11]([C:8]2[CH:7]=[CH:6][C:5]([C:4]([OH:3])=[O:20])=[CH:10][CH:9]=2)[CH:12]=1)#[N:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59477905HCID 59477905, compound

Product 1

HCID 59478027HCID 59478027, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3-cyano-4-hydroxymethylpyrrole-1-yl)benzoic acid ethyl ester (0.022 g) in tetrahydrofuran (1 mL) were added triethylamine (0.0082 g) and methane sulfonylchloride (0.0093 g) under ice-cooling. After warming to ambient temperature, this mixture was stirred for 30 minutes. The insoluble material of this reaction mixture was removed by filtration, and this filtrate was added to a mixture of ethanol (1.125 g) and sodium hydride (60%, 0.13 g), and this mixture was stirred for 5 hours. To this reaction mixture was added water, and this mixture was stirred at room temperature for 1 hours. To this reaction mixture was added 2 mol/L hydrochloric acid (3 mL), this mixture was extracted with ethyl acetate. This organic layer was washed with brine, concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=88/12−81/19) to give the title compound (0.010 g).

Workup

  1. temperaturecooling
  2. customThe insoluble material of this reaction mixture was removed by filtration
  3. additionthis filtrate was added to a mixture of ethanol (1.125 g) and sodium hydride (60%, 0.13 g)
  4. stirringthis mixture was stirred for 5 hours
  5. additionTo this reaction mixture was added water
  6. stirringthis mixture was stirred at room temperature for 1 hours
  7. additionTo this reaction mixture was added 2 mol/L hydrochloric acid (3 mL)
  8. extractionthis mixture was extracted with ethyl acetate
  9. washThis organic layer was washed with brine
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=88/12−81/19)

Sources & evidence

ORD record
ord-83fb8101359e43c3b3896d7f8c53f171
Source dataset
uspto-grants-2012_07
Patent number
US08227500B2

Reaction notes

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