Reaktion #1131955

Reaktionsgleichung

N2

2-{[(tert-butyldimethylsilyl)oxy]methyl}-4-(2-methyl-[1,3]dioxolan-2-yl)oxazole

TBAF

NH4Cl

→

title compound

(4-(2-Methyl-[1,3]dioxolan-2-yl)-oxazol-2-yl)-methanol

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe layers separated
2. 2
   Extraktionthe aq. layer extracted with EA
3. 3
   Trocknenextracts were dried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigePurification of the residue by FC (2:3 to 1:0 EA-Hept)

Vorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-{[(tert-butyldimethylsilyl)oxy]methyl}-4-(2-methyl-[1,3]dioxolan-2-yl)oxazole (3.50 g, 11.69 mmol) in dry THF (70 mL) was treated at 0° C. with TBAF (15.2 mL of a 1M solution in THF, 15.20 mmol). The reaction mixture was stirred at 0° C. for 1 h. Sat. aq. NH4Cl was added, the layers separated and the aq. layer extracted with EA. The combined org. extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. Purification of the residue by FC (2:3 to 1:0 EA-Hept) gave the title compound as a pale yellow oil. TLC: rf (EA)=0.20. LC-MS-conditions 01: tR=0.45 min, [M+H]+=186.00.

Quelle