Réaction #1859585

Équation de réaction

p-toluenesulfonic acid monohydrate

compound 14

4-(3,5-Di-tert-butylphenyl)-2-((1-methylcyclohexyl)methyl)-2,3-dihydro-1H-inden-1-ol

→

compound 15

Rendement 81.0%

7-(3,5-Di-tert-butylphenyl)-2-((1-methylcyclohexyl)methyl)-1H-indene

Rendement 81.0%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   Températurewas refluxed for 1 h
2. 2
   Lavagethe mixture was washed sequentially with saturated sodium bicarbonate (100 mL) and saturated brine (100 mL)
3. 3
   SéchageThe organic layer dried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   AutreThe residue was purified on an AnaLogix (65-200 g) column
7. 7
   Lavageeluting with heptanes

Mode opératoire

A mixture of p-toluenesulfonic acid monohydrate (0.88 g, 4.64 mmol, 0.2 equiv), compound 14 (10.0 g crude, 23.22 mmol, 1.0 equiv) and toluene (200 mL) was refluxed for 1 h. After cooling to room temperature, the mixture was washed sequentially with saturated sodium bicarbonate (100 mL) and saturated brine (100 mL). The organic layer dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified on an AnaLogix (65-200 g) column, eluting with heptanes to give compound 15 (7.8 g, 81% yield for 2 steps) as a white solid.

Source