Sodium borohydride → Thieno[2,3-b]pyrazin-6-ylmethanol

HRID 1184859Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1184859
[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[S:7][C:8]([C:10](OCC)=[O:11])=[CH:9][C:2]=12.[BH4-].[Na+]>C1COCC1.CO.[NH4+].[Cl-]>[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[S:7][C:8]([CH2:10][OH:11])=[CH:9][C:2]=12

Komponenten

6

Edukt 2

HCID 4311764Sodium borohydrideHCID 12299125Ethyl thieno[2,3-b]pyrazine-6-carboxylate

Produkt 1

HCID 67125540Thieno[2,3-b]pyrazin-6-ylmethanolAusbeute 91,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To a solution of ethyl thieno[3,2-b]pyrazine-6-carboxylate 86 (600 mg, 2.88 mmol) in THF (3 mL) and methanol (3 mL) was added sodium borohydride (1.09 g, 28.8 mmol). The reaction was stirred at rt for 30 min. Poured in NH4Cl solution and extracted with EtOAc. Organic layer was washed with brine, dried and evaporated to give the crude thieno[3,2-b]pyrazin-6-ylmethanol 87 (438 mg, 91%) which was used without further purification.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washOrganic layer was washed with brine
  3. customdried
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1e7969c25aee441cad9518918c62efb9
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669256B2

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