Reaktion #1547462

Reaktionsgleichung

diethyl azodicarboxylate

3,3-dimethyl-4-pentyn-1-ol

4-chlorophenol

triphenyl phosphine

→

colorless crystalline solid

Ausbeute 50.3%

5-(4-chlorophenoxy)-3,3-dimethyl-1-pentyne

Ausbeute 50.3%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent is evaporated
2. 2
   Sonstigethe residue triturated with hexane
3. 3
   FiltrationThe solid is filtered
4. 4
   Waschenwashed with hexane
5. 5
   Sonstigethe resulting filtrate evaporated
6. 6
   Waschenas eluting solvent

Vorschrift

To a solution of 5.0 g (44.6 mmol) of 3,3-dimethyl-4-pentyn-1-ol and 5.7 g (44.6 mmol) of 4-chlorophenol in 125 ml of tetrahydrofuran cooled to 0° C. is added 11.7 g (44.6 mmol) of triphenyl phosphine followed by 7.8 g (7.0 ml, 44.6 mmol) of diethyl azodicarboxylate. The reaction mixture is allowed to warm to room temperature and stirred overnight. The solvent is evaporated and the residue triturated with hexane. The solid is filtered, washed with hexane and the resulting filtrate evaporated. The residue is subjected to flash chromatography (silica gel) using hexane as eluting solvent to afford 5.0 g of colorless crystalline solid: m.p. 42°-45° C.; NMR (CDCl3) δ1.3 (6H, s), 1.9 (2H, t, J=6.5 Hz), 2.12 (1H, s), 4.15 (2H, t, J=6.6 Hz), 6.8 (2H, d, J=9.0 Hz), 7.2 (2H, d, J=9.0 Hz).

Quelle