1,2,3,5-Tetrahydro-6-methyl-4-phenyl-s-indacene synthesis
- Product Name:1,2,3,5-Tetrahydro-6-methyl-4-phenyl-s-indacene
- CAS Number:852160-02-2
- Molecular formula:C19H18
- Molecular Weight:246.35
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Yield:852160-02-2 87%
Reaction Conditions:
with toluene-4-sulfonic acid in toluene; for 3 h;Heating / reflux;
Steps:
1.1e
3,5,6,7-tetrahydro-2-methyl-4-phenyl-s-hydraindacen-1(2H)-ol (2.46 g, 9.29 mmol) was dissolved in toluene (100 mL) and p-toluenesulfonic acid (0.12 g) was added. The resulting solution was heated to reflux for 3 hours, then washed with saturated aqueous NaHCO3 (2 x 50 mL), dried over MgSO4, filtered, and dried under dynamic vacuum, giving 2.0 g, 87 percent of the corresponding indacene. A 125 mL glass flask was charged with the indacene (1.045 g) and 50 mL mixed hexanes. To this was then added 2.65 mL of n-butyllithium in mixed hexanes. After one hour, the mother liquor was decanted from the precipitate that had formed. The precipitate was dissolved in 30 mL of tetrahydrofuran (THF). To this solution, dimethyl (t- butylamino) silylchloride (0.800g in 5 mL THF) was added and the resulting mixture stirred overnight. The volatiles were removed under dynamic vacuum and the residue extracted with mixed hexanes (50 mL), filtered and the volatiles again removed under dynamic vacuum, giving 1.42 g (105 percent) of the desired product along with residual solvent.
References:
WO2004/13149,2004,A1 Location in patent:Page/Page column 14
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