Methanol → Methyl 2-(5-((tert-butyldimethylsilyloxy)methyl)thiophen-2-yl)acetate

HRID 1944156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1944156
[Si:1]([O:8][CH2:9][C:10]1[S:14][C:13]([CH2:15][C:16]([OH:18])=[O:17])=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:19]O>>[Si:1]([O:8][CH2:9][C:10]1[S:14][C:13]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

3

Edukt 2

HCID 887MethanolHCID 595637742-(5-((Tert-butyldimethylsilyloxy)methyl)thiophen-2-yl)acetic acid

Produkt 1

HCID 59563701Methyl 2-(5-((tert-butyldimethylsilyloxy)methyl)thiophen-2-yl)acetate

Versuchsvorschrift

To 2-(5-((tert-butyldimethylsilyloxy)methyl)thiophen-2-yl)acetic acid (E231) in MeOH at 0° C. was added TMS-CH2N2 until the solution persisted in a yellow color and TLC indicated completion of the reaction. The solution stirred for 30 min and then was quenched with a few drops of AcOH. The solvents were evaporated and column chromatography (SiO2, 0-15% EtOAc/Hexanes) gave pure methyl 2-(5-((tert-butyldimethylsilyloxy)methyl)thiophen-2-yl)acetate (E232).

Aufarbeitung

  1. customcompletion of the reaction
  2. customwas quenched with a few drops of AcOH
  3. customThe solvents were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-a693824ed703419c9778bd292faa5ad4
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394826B2

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