Methanol → HCID 86615211, compound

HRID 733750Notes

Reaction equation

HRID 733750 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]([O:12][CH3:13])=[O:11])=[C:5]1[CH2:14][C:15]([O:17][CH3:18])=[O:16].[CH:19](OC)=[O:20].CO>O1CCCC1>[CH:19]([CH:14]([C:5]1[N:4]([CH3:3])[C:8]([CH3:9])=[CH:7][C:6]=1[C:10]([O:12][CH3:13])=[O:11])[C:15]([O:17][CH3:18])=[O:16])=[O:20]

Participants

6

Reactant 4

HCID 887Methanol3×HCID 7865Methyl formateHCID 24758Sodium hydrideHCID 57841007HCID 57841007, compound

Product 1

HCID 86615211HCID 86615211, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

Sodium hydride (2.29 g, 60% dispersion in mineral oil) was added portionwise to a stirred solution of methyl 1,5-dimethyl-2-[2-(methyloxy)-2-oxoethyl]-1H-pyrrole-3-carboxylate (2.37 g) in tetrahydrofuran (30 ml) at 20° C. After fifteen minutes the reaction mixture was cooled to 10° C. and methyl formate (1.0 ml) added. After ten minutes a mixture of methanol (0.05 ml) and tetrahydrofuran (1 ml) was added. The reaction mixture was stirred at room temperature for sixteen hours. After cooling to 10° C., methanol (0.1 ml) was added, the mixture was stirred at room temperature for two hours. After cooling in an ice bath, methanol (8.4 ml) was added dropwise, the mixture was stirred for a further fifteen minutes, then evaporated. The residue was partitioned between ethyl acetate and aqueous ammonium chloride, and then acidified by addition of 5N hydrochloric acid. The aqueous phase was extracted with a second portion of ethyl acetate. The combined organic extracts were washed with water, then brine, dried (MgSO4) and evaporated. The solid residue washed with hexane and then dried to give the title compound 2.59 g as a tautomeric mixture.

Workup

  1. additionwas added
  2. temperatureAfter cooling to 10° C.
  3. stirringthe mixture was stirred at room temperature for two hours
  4. temperatureAfter cooling in an ice bath
  5. stirringthe mixture was stirred for a further fifteen minutes
  6. customevaporated
  7. customThe residue was partitioned between ethyl acetate and aqueous ammonium chloride
  8. additionacidified by addition of 5N hydrochloric acid
  9. extractionThe aqueous phase was extracted with a second portion of ethyl acetate
  10. washThe combined organic extracts were washed with water
  11. dry with materialbrine, dried (MgSO4)
  12. customevaporated
  13. washThe solid residue washed with hexane
  14. customdried

Sources & evidence

ORD record
ord-40ac9b72bb724a5aaa0e11bdd37841fd
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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