Aluminium lithium hydride → (1-((Trimethylsilyl)methyl)-1h-1,2,3-triazol-4-yl)methanol

HRID 509300

Reaktionsgleichung

[CH3:1][Si:2]([CH2:5][N:6]1[CH:10]=[C:9]([C:11](OCC)=[O:12])[N:8]=[N:7]1)([CH3:4])[CH3:3].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:4][Si:2]([CH2:5][N:6]1[CH:10]=[C:9]([CH2:11][OH:12])[N:8]=[N:7]1)([CH3:1])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A solution of ethyl 1-[(trimethylsilyl)methyl]-1H-1,2,3-triazole-4-carboxylate (1.00 g, 4.40 mmol) and THF (14.6 mL) was cooled to 0° C. and a solution of LAH (4.40 mL, 1M in THF) was added dropwise. The mixture was stirred for 1 h, and the cold bath was removed and stirred for an additional hour. The reaction was cooled to 0° C. and a solution of saturated sodium sulfate (4.4 mL) was added. The mixture was warmed to room temperature, stirred 30 min, and filtered. The filtrate was concentrated and the residue azeotroped with ethanol to afford a colorless oil purified via MPLC, 40M column, 1-8% MeOH in DCM afforded the title material as a clear, colorless oil. MS: cal'd 186 (MH+), exp 186 (MH+).

Aufarbeitung

customthe cold bath was removed
stirringstirred for an additional hour
additiona solution of saturated sodium sulfate (4.4 mL) was added
temperatureThe mixture was warmed to room temperature
stirringstirred 30 min
filtrationfiltered
concentrationThe filtrate was concentrated
customthe residue azeotroped with ethanol
customto afford a colorless oil
custompurified via MPLC, 40M column, 1-8% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag: ord-b0fc0ec635994b9482bc2e9cf83c03ac
Quelldatensatz: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09096559B2

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