Reaktion #1363882

Reaktionsgleichung

NaH

toluene

cyclopentanol

9-bromoanthracene

toluene

→

9-anthryl cyclopentyl ether

Ausbeute 68.6%

Lösungsmittel

brine

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAn oven dried Schlenk tube
2. 2
   Sonstigeequipped with a teflon coated stir bar
3. 3
   workup.ADDITIONback-filled with argon
4. 4
   workup.ADDITIONwere added
5. 5
   SonstigeThe organic layer was separated
6. 6
   Trocknendried over anhydrous MgSO4
7. 7
   SonstigeThe drying agent was removed by filtration
8. 8
   Einengenthe mother liquor concentrated in vacuo
9. 9
   SonstigeThe crude product was purified by flash chromatography on silica gel (99:1 hexanes:ethyl acetate)

Vorschrift

An oven dried Schlenk tube equipped with a teflon coated stir bar was charged with NaH (60% dispersion in mineral oil, 60 mg, 1.50 mmol), placed under vacuum and back-filled with argon. To this was added toluene (2 mL) and cyclopentanol (109 μL, 0.90 mmol). The mixture was heated at 70° C. for 15 min at which time 9-bromoanthracene (193 μL, 0.75 mmol), Pd2 (dba)3 (10.3 mg, 0.0113 mmol), (R)-(+)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl (Tol-BINAP) (18.3 mg, 0.027 mmol), and 2 mL of toluene were added. The mixture was heated at 100° C. under an atmosphere of argon. After 20 hours diethyl ether (30 mL) and brine (30 mL) were added. The organic layer was separated and dried over anhydrous MgSO4. The drying agent was removed by filtration and the mother liquor concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (99:1 hexanes:ethyl acetate) to afford 9-anthryl cyclopentyl ether (135 mg, 68% yield) as a yellow solid

Quelle