Réaction #1859590

Équation de réaction

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

Rendement 67.0%

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

Rendement 67.0%

Solvants

toluene

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source