Reaktion #48334

Reaktionsgleichung

(4R)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-ol

diphenylphosphoryl azide

1,8-diazabicyclo(5.4.0)undec-7-ene

→

title compound

(4S)-4-azido-6-bromo-2-methyl-2-(trifluoromethyl)chroman

Lösungsmittel

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction was stirred at the same temperature for 2 h
2. 2
   Sonstigeto quench
3. 3
   Sonstigethe reaction
4. 4
   ExtraktionThe resulted mixture was extracted with EtOAc
5. 5
   WaschenThe organics were washed with brine
6. 6
   Trocknendried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   SonstigeThe residue was purified on a silica gel column (5-20% EtOAc/hexane)

Vorschrift

To a cooled (ice bath) solution of (4R)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-ol (277 mg, 890 μmol) was added drop wise diphenylphosphoryl azide (249 μl, 1158 μmol). After stirring 20 min, 1,8-diazabicyclo(5.4.0)undec-7-ene (173 μl, 1158 μmol) was added drop wise. The reaction was stirred at the same temperature for 2 h, then stirred 15h at ambient temperature. Water was added to quench the reaction. The resulted mixture was extracted with EtOAc. The organics were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified on a silica gel column (5-20% EtOAc/hexane) to afford the title compound. MS m/z: 308(M−N2).

Quelle