1-(3,5-di-tert-butylphenyl)ethanone synthesis
- Product Name:1-(3,5-di-tert-butylphenyl)ethanone
- CAS Number:1756-31-6
- Molecular formula:C16H24O
- Molecular Weight:232.36
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Yield: 85%
Reaction Conditions:
in tetrahydrofuran;diethyl ether at -78 - 20;
Steps:
5.1.1. 1-(3,5-Di-tert-butylphenyl)ethanone (15)
1.6 N MeLi in Et2O (300 μL, 0.480 mmol) was added to a solution of 14 (50.7 mg, 0.0216 mmol) in THF (1.0 mL) at -78 °C. The mixture was stirred at room temperature for 5 h, then poured into water and extracted with AcOEt. The organic layer was washed with brine and dried over MgSO4. Filtration, evaporation of the solvent in vacuo and purification by flash column chromatography (AcOEt/n-hexane = 1/25) gave 42.5 mg (85%) of 15 as a yellow oil; 1H NMR (CDCl3, 500 MHz, δ; ppm) 7.81 (2H, d, J = 1.8 Hz), 7.65 (1H, t, J = 1.8 Hz), 2.63 (3H, s), 1.36 (18H, s); MS (FAB) m/z: 233 (MH+).
References:
Itoh, Yukihiro;Kitaguchi, Risa;Ishikawa, Minoru;Naito, Mikihiko;Hashimoto, Yuichi [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 22,p. 6768 - 6778] Location in patent:experimental part
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