Dimethyl Sulfate → HCID 68155916, compound

HRID 1877785Notes

Reaction equation

HRID 1877785 reaction equation
S(OC)(O[CH3:5])(=O)=O.[CH2:8]([O:10][C:11]([C:13]1[NH:14][CH:15]=[C:16]([CH3:19])[C:17]=1[OH:18])=[O:12])[CH3:9].[OH-].[Na+]>O>[CH3:5][O:18][C:17]1[C:16]([CH3:19])=[CH:15][NH:14][C:13]=1[C:11]([O:10][CH2:8][CH3:9])=[O:12]

Participants

5

Reactant 3

HCID 6497Dimethyl Sulfate3×HCID 14798Sodium HydroxideHCID 68155946HCID 68155946, compound

Product 1

HCID 68155916HCID 68155916, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add dimethyl sulfate (3 mL, 3.99 g, 31.63 mmoles) to a mixture of 3-hydroxy-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (3.5 g, 20.69 mmoles) and 2M sodium hydroxide (75 mL, 1500 mmoles) and stir the reaction mixture vigorously for 30 mins at room temp (water cooling bath applied). Collect the resultant precipitate and wash with water. Add more dimethyl sulfate (3 mL, 3.99 g, 31.63 mmoles) to the filtrate and stir for 30 minutes. Collect the resultant precipitate and wash with water. Add more dimethyl sulfate (3 mL, 3.99 g, 31.63 mmoles) to the filtrate and stir for 1 h. Combine the isolated precipitates and dry in a vacuum oven at 50° C. for 30 minutes to give ethyl 3-methoxy-4-methyl-1H-pyrrole-2-carboxylate (3.221 g, 84.98% yield). MS (m/z): 184.09 (M+1).

Workup

  1. customCollect the resultant precipitate
  2. washwash with water
  3. customCollect the resultant precipitate
  4. washwash with water
  5. stirringstir for 1 h
  6. customprecipitates
  7. customdry in a vacuum oven at 50° C. for 30 minutes

Sources & evidence

ORD record
ord-f57485c69ada43519a640f5cd8d9f870
Source dataset
uspto-grants-2012_11
Patent number
US08314092B2

Reaction notes

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