Ammonium Chloride → methyl 5-(hydroxymethyl)-1-methyl-1H-pyrrole-2-carboxylate

HRID 1009474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009474
[CH:1]([C:3]1[N:7]([CH3:8])[C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+].[Cl-].[NH4+]>C1COCC1>[OH:2][CH2:1][C:3]1[N:7]([CH3:8])[C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 12459974methyl 5-formyl-1-methyl-1H-pyrrole-2-carboxylate

Produkt 1

HCID 58009357methyl 5-(hydroxymethyl)-1-methyl-1H-pyrrole-2-carboxylateAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

670 mg of methyl 5-formyl-1-methyl-1H-pyrrole-2-carboxylate was dissolved in 10.0 mL of THF, and 303 mg of sodium borohydride was added thereto at −20° C., followed by stirring at −20° C. for 30 minutes, and then at 0° C. for further 1 hour. To the reaction liquid was added an aqueous saturated ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution and brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 592 mg of methyl 5-(hydroxymethyl)-1-methyl-1H-pyrrole-2-carboxylate.

Aufarbeitung

  1. customat −20° C.
  2. waitat 0° C. for further 1 hour
  3. customTo the reaction liquid
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1083655ced704d539f6868bc191c9cc1
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973078B2

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