Reaktion #510064

Reaktionsgleichung

KHMDS

2-(4-(benzyloxy)phenyl)-2-(2,6-difluorophenyl)cycloheptanone

→

title compound 22

(E)-10a-(4-(Benzyloxy)phenyl)-1-fluoro-8,9,10,10a-tetrahydro-7H-benzo[b]-cyclohepta[d]furan

Lösungsmittel

toluene

DMPU

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAdditional heating for 1 h
2. 2
   Sonstigegave no further conversion of the starting material
3. 3
   WaschenThe organic phase was washed with water (10 mL), brine
4. 4
   Trocknendried (Na2SO4)
5. 5
   Einengenconcentrated in vacuo

Vorschrift

KHMDS (0.2 mL, 0.5 M in toluene) was added to a solution of 2-(4-(benzyloxy)phenyl)-2-(2,6-difluorophenyl)cycloheptanone (50 mg) in toluene (3 mL) and DMPU (1 mL). The reaction mixture was heated at 90° C. for 2 h (TLC indicated some conversion of the starting material). Additional heating for 1 h gave no further conversion of the starting material according to TLC. The organic phase was washed with water (10 mL), brine, dried (Na2SO4) and concentrated in vacuo. Work-up by flash chromatography (eluent heptane dichloromethane 1:1) afforded the title compound 22 in a yield of 20 mg. 1H-NMR (400 MHz, CDCl3): δ ppm 7.49-7.46 (m, 2H), 7.50-7.34 (m, 5H), 7.10-7.00 (m, 1H), 6.96-6.91 (m, 2H), 6.61-6.59 (m, 1H), 6.53-6.48 (m, 1H), 5.73 (dd, J=5, 9 Hz, 1H), 5.02 (s, 2H), 3.07-3.02 (m, 1H), 2.00-1.20 (m, 8H).

Quelle