Reaktion #2371655

Reaktionsgleichung

alcohol

4-bromo-2-fluoro-5-(hydroxymethyl)phenol

4-bromo-2-fluoro-5-(hydroxymethyl)phenol

3,4 dihydro-2H-pyran

→

2-(4-bromo-2-fluoro-5-((tetrahydro-2H-pyran-2-yloxy)methyl)phenoxy)tetrahydro-2H-pyran

Ausbeute 83.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was then quenched with equal volumes of 0.2 M NaOH and EtOAc (1:1, 20 mL) before the layers
2. 2
   Sonstigewere separated
3. 3
   ExtraktionThe water phase was further extracted with equal volume of EtOAc before the organic layers
4. 4
   Trocknendried over anhydrous Na2SO4
5. 5
   Filtrationfiltered
6. 6
   SonstigeThe solvent was removed under reduced pressure
7. 7
   SonstigeThe residue was purified by silica gel column

Vorschrift

Protection of the alcohol was carried out by making a solution of 4-bromo-2-fluoro-5-(hydroxymethyl)phenol (1.37 g, 6.19 mmol), 3,4 dihydro-2H-pyran (1.4 mL, 15 mmol) in 20 mL of CH2Cl2. The reaction mixture was then treated with camphor sulfonic acid (58 mg, 0.25 mmol) before stirring at room temperature for 21 hr. The reaction mixture was then quenched with equal volumes of 0.2 M NaOH and EtOAc (1:1, 20 mL) before the layers were separated. The water phase was further extracted with equal volume of EtOAc before the organic layers were combined and dried over anhydrous Na2SO4 and filtered. The solvent was removed under reduced pressure. The residue was purified by silica gel column using Combiflash to give 2-(4-bromo-2-fluoro-5-((tetrahydro-2H-pyran-2-yloxy)methyl)phenoxy)tetrahydro-2H-pyran (2.0 g, 83%).

Quelle