2-[2-(6-methoxytetralin-1-ylidene)-ethyl]-2-methylcyclopentane-1,3-dione synthesis
- Product Name:2-[2-(6-methoxytetralin-1-ylidene)-ethyl]-2-methylcyclopentane-1,3-dione
- CAS Number:899-79-6
- Molecular formula:C19H22O3
- Molecular Weight:298.3762
Yield:899-79-6 73%
Reaction Conditions:
Stage #1: 2-Methylcyclopentane-1,3-dione;6-methoxy-1-vinyl-1,2,3,4-tetrahydronaphthalen-1-ol in 5,5-dimethyl-1,3-cyclohexadiene;tert-butyl alcohol at 20; for 0.25 h;Inert atmosphere;
Stage #2: with N-benzyl-trimethylammonium hydroxide in methanol;5,5-dimethyl-1,3-cyclohexadiene;tert-butyl alcohol; for 2 h;Inert atmosphere;Reflux;
Steps:
The vinyl carbinol 1s (4.1 g, 20 mmol, 1 equiv) was dissolved in a 2/1 mixture of xylene/tBuOH(c = 0.6 M). 2-methylcyclopentane-1,3-dione (3.3 g, 30 mmol, 1.5 equiv) was added and, after stirring15 min at room temperature, a 40% solution of Triton B in MeOH (2 mL, 4 mmol, 0.2 equiv) wasadded. The mixture was stirred under reflux for 12 h. At 0 °C Et2O (5 mL/1 mmol of SM) was addedand the mixture was stirred at 0 °C for 30 min. The mixture was filtrated and washed with Et2O. Thecombined filtrates were washed with a 5% potassium hydroxide solution (3 times) and with water (3times), dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (Al2O3 activity I, hexane/EtOAc) , the title compound 2s was isolated in 73% yield(5.3 g) as a yellow oil.
References:
Ye, Yang;Ma, Guobin;Yao, Ken;Gong, Hegui [Synlett,2021,vol. 32,# 16,art. no. ST-2020-K0570-C,p. 1625 - 1628] Location in patent:supporting information
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