Reaktion #313386

Reaktionsgleichung

4-bromo-1-methoxy-2-methylindane

1-methoxy-2-methyl-4-indanol

K3PO4

2-di(tert-butyl)phosphino-2′-(N,N-dimethylamino)biphenyl

→

1-Methoxy-4-[(1-methoxy-2-methyl-2,3-dihydro-1H-inden-4-yl)oxy]-2-methylindane

Lösungsmittel

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added under an argon atmosphere
2. 2
   SonstigeThe organic layer was separated
3. 3
   Extraktionthe aqueous layer was extracted with 3×100 ml of CH2Cl2
4. 4
   ExtraktionThe combined extract
5. 5
   Waschenwas washed with 2×100 ml of water
6. 6
   Trocknendried over K2CO3
7. 7
   Sonstigeevaporated to dryness
8. 8
   SonstigeThe analytically pure product was obtained
9. 9
   workup.ADDITIONOn the evidence of NMR spectra, the product consists of a mixture of isomers

Vorschrift

To a mixture of 14.6 g (60.5 mmol) of 4-bromo-1-methoxy-2-methylindane, 10.8 g (60.5 mmol) of 1-methoxy-2-methyl-4-indanol, 38.5 g (181 mmol) K3PO4, and 200 ml of toluene, a mixture of 696 mg (1.21 mmol) Pd(dba)2 and 825 mg (2.42 mmol) of 2-di(tert-butyl)phosphino-2′-(N,N-dimethylamino)biphenyl was added under an argon atmosphere. This mixture was stirred for 14 hours at 100° C. Then, 300 ml of water was added. The organic layer was separated, and the aqueous layer was extracted with 3×100 ml of CH2Cl2. The combined extract was washed with 2×100 ml of water, dried over K2CO3, and evaporated to dryness. The analytically pure product was obtained using flash chromatography on Silica Gel 60 (40-63 μm, d 50 mm, 1 400 mm, eluant:hexanes-dichloromethane=1:1, vol.). Yield 12.4 g (61%). On the evidence of NMR spectra, the product consists of a mixture of isomers.

Quelle