1-Penten-3-one, 1-(4-methoxyphenyl)-4-methyl- synthesis
- Product Name:1-Penten-3-one, 1-(4-methoxyphenyl)-4-methyl-
- CAS Number:103-13-9
- Molecular formula:C13H16O2
- Molecular Weight:204.27
689258-25-1
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103-13-9
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Yield:103-13-9 79%
Reaction Conditions:
with trifluorormethanesulfonic acid in dichloromethane at 20; for 1 h;Inert atmosphere;
Steps:
Typical experimental procedure for a reaction intramolecular cycloisomerization
General procedure: To a stirred solution of 2,2-dimethyl-3-phenylcyclobutanone (1a) (50 mg, 0.29 mmol) in dry dichloromethane (2 mL) was added TfOH (0.13 mL, 1.45 mmol) at room temperature. The resulting solution was stirred for 1 h and the reaction was quenched by adding aqueous solution of NaHCO3. The resulting mixture was extracted with dichloromethane (3×10 mL) and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by column chromatography on silica gel (hexane/ethyl acetate = 20:1) to afford 4a (37.5 mg, 0.215mmol, 75%).
References:
Kanie, Mayu;Ikawa, Yuya;Yoshimura, Tomoyuki;Matsuo, Jun-ichi [Tetrahedron Letters,2019,vol. 60,# 32,art. no. 150910] Location in patent:supporting information
