Reaktion #1384970

Reaktionsgleichung

tetrabutylammonium fluoride

3,3-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-1,3-dihydro-indol-2-one

triethylamine

HCl

4-(trifluoromethyl)phenylboronic acid

→

title compound

Ausbeute 59.0%

3,3-Bis-(4-hydroxy-3,5-dimethyl-phenyl)-1-(4-trifluoromethyl-phenyl)-1,3-dihydro-indol-2-one

Ausbeute 59.0%

Lösungsmittel

THF

dichloromethane

THF

ethyl acetate

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationFilter
2. 2
   Sonstigethe reaction through Celite
3. 3
   WaschenElute through a column of silica gel with 70% dichloromethane in hexanes
4. 4
   Einengenconcentrate
5. 5
   workup.STIRRINGStir for 1 h
6. 6
   SonstigeSeparate the layers
7. 7
   Einengenconcentrate the organic layer in vacuo

Vorschrift

Combine 3,3-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-1,3-dihydro-indol-2-one (0.561 g, 0.932 mmol), 4-(trifluoromethyl)phenylboronic acid (0.354 g, 1.86 mmol), copper (II) acetate (0.169 g, 0.932 mmol), triethylamine (0.26 mL, 1.86 mmol), 4 angstrom molecular sieves, and dichloromethane (15 mL). Stir at room temperature overnight under ambient atmosphere. Filter the reaction through Celite. Elute through a column of silica gel with 70% dichloromethane in hexanes and concentrate. Dissolve the resulting compound (0.498 g, 0.667 mmol), in THF (4 mL). Add a solution of tetrabutylammonium fluoride (1.0 M) in THF (1.80 mL). Stir for 1 h. Add 1N aqueous HCl(10 mL), water (40 mL), and ethyl acetate (50 mL). Separate the layers and concentrate the organic layer in vacuo. Chromatograph on silica gel eluting with ethyl acetate to give 0.283 g (59%) of the title compound: mass spectrum (FAB): m/z=518(M+1); 1H NMR(DMSO-d6): δ8.32 (s, 2H), 7.98 (d, 2H), 7.79 (d, 2H), 7.40 (d, 1H), 7.32 (td, 1H), 7.21 (td, 1H), 6.99 (d, 1H), 6.80 (s, 4H), 2.13 (s, 12H).

Quelle