Reaktion #1859590

Reaktionsgleichung

p-toluene-sulfonic acid monohydrate

compound 22

4-([1,1′-Biphenyl]-2-yl)-2-((1-methylcyclohexyl)methyl)-2,3-dihydro-1H-inden-1-ol

→

compound 23

Ausbeute 67.0%

7-([1,1′-Biphenyl]-2-yl)-2-((1-methylcyclohexyl)methyl)-1H-indene

Ausbeute 67.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 1 hour
2. 2
   Waschenthe mixture was washed sequentially with saturated sodium bicarbonate (100 mL) and saturated brine (100 mL)
3. 3
   TrocknenThe organic layer was dried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe residue was purified on an AnaLogix (25-80 g) column
7. 7
   Wascheneluting with a gradient of 0 to 10% ethyl acetate in heptanes

Vorschrift

Mixture of p-toluene-sulfonic acid monohydrate (0.38 g, 2.0 mmol, 0.2 equiv), compound 22 (4.0 g crude, ˜9.88 mmol, 1.0 equiv) and toluene (100 mL) was refluxed for 1 hour. After cooling to room temperature, the mixture was washed sequentially with saturated sodium bicarbonate (100 mL) and saturated brine (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified on an AnaLogix (25-80 g) column, eluting with a gradient of 0 to 10% ethyl acetate in heptanes to give compound 23 (2.5 g, 67% yield for 2 steps) as a white solid.

Quelle