Hydrochloric Acid → 4-Formyl-1-methanesulfonyl-1H-pyrrole-2-carboxylic acid methyl ester

HRID 2249515Notes

Reaction equation

HRID 2249515 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[NH:9][CH:8]=[C:7]([CH:10]=[O:11])[CH:6]=1)=[O:4].[H-].[Na+].[CH3:16][S:17](Cl)(=[O:19])=[O:18].Cl.[CH3:22][OH:23]>C(N(CC)CC)C>[CH3:22][O:23][C:3]([C:5]1[N:9]([S:17]([CH3:16])(=[O:19])=[O:18])[CH:8]=[C:7]([CH:10]=[O:11])[CH:6]=1)=[O:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 124599775-Trichloroacetyl-1H-pyrrole-3-carbaldehyde

Product 1

HCID 596397074-Formyl-1-methanesulfonyl-1H-pyrrole-2-carboxylic acid methyl esterYield 82%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 5-trichloroacetyl-1H-pyrrole-3-carbaldehyde (3.6 g, 14.97 mmol) in MeOH (60 mL) was added triethylamine (2 mL). The reaction mixture was stirred at room temperature for 3 hours. The solvent was removed and the residue was dried on the vacuum pump for 6 hours. This crude product was then dissolved in 60 mL of anhydrous THF. To the resulting solution was added NaH (720 mg, 18 mmol) at room temperature. The suspension was then stirred at room temperature for 1 hour before addition of MsCl (2.6 g, 22.70 mmol). The mixture was left at room temperature overnight and then poured into 2N HCl solution (100 mL). The aqueous solution was extracted with EtOAc (3×60 mL), the combined organic layers were dried over MgSO4, the solvent was removed by evaporation, and the residue was purified by flash column eluting with 30% EtOAc/hexanes to afford the title compound as a white solid (2.85 g, 82%). 1H NMR (500 MHz, DMSO-d6) δ9.88 (s, 1H), 8.40 (s, 1H), 7.40 (s, 1H), 3.96 (s, 3H), 3.85 (s, 3H) ppm. MS (ES+): m/e=232.1 (M+H); LC/Method A/2.61 min.

Workup

  1. customThe solvent was removed
  2. customthe residue was dried on the vacuum pump for 6 hours
  3. dissolutionThis crude product was then dissolved in 60 mL of anhydrous THF
  4. waitThe mixture was left at room temperature overnight
  5. extractionThe aqueous solution was extracted with EtOAc (3×60 mL)
  6. dry with materialthe combined organic layers were dried over MgSO4
  7. customthe solvent was removed by evaporation
  8. customthe residue was purified by flash column
  9. washeluting with 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-469c83b879ca4b0394d61b17afaa4072
Source dataset
uspto-grants-2008_01
Patent number
US07314885B2

Reaction notes

Loading…