Sodium borohydride → Methyl 2-(hydroxymethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

HRID 1409426Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1409426
[CH:1]([C:3]1[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[N:7]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:17])([CH3:19])[CH3:18])[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[N:7]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 58638526methyl 2-formyl-1-((2-(trimethylsilyl)-ethoxy)-methyl)-1H-imidazole-4-carboxylate

Produkt 1

HCID 70980902Methyl 2-(hydroxymethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Into a flask containing a solution of methyl 2-formyl-1-((2-(trimethylsilyl)-ethoxy)-methyl)-1H-imidazole-4-carboxylate (3 g, 10.5 mmol) in MeOH (20 ml), NaBH4 (0.401 g, 10.5 mmol) was added in portions at 0° C. The resulting mixture was allowed to stir at 0° C. for 30 min followed by RT for 1 hour. The reaction mixture was concentrated and the crude was diluted with water and extracted with EtOAc. The organic layer was concentrated under reduced pressure. Yield 1.5 g. LC-MS: [M+1]=287.17.

Aufarbeitung

  1. additionwas added in portions at 0° C
  2. waitfollowed by RT for 1 hour
  3. concentrationThe reaction mixture was concentrated
  4. additionthe crude was diluted with water
  5. extractionextracted with EtOAc
  6. concentrationThe organic layer was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5343b9fe06724720a7c313978e2712a2
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921378B2

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