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For a review of [3+3] cyclocondensations of 1,3-bis(silyl enol ethers) with 1,3-dielectrophiles, see: Feist, H.; Langer, P. Synthesis 2007, 327.
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For a review of [3+3] cyclocondensations of 1,3-bis(silyl enol ethers) with 1,3-dielectrophiles, see: Feist, H.; Langer, P. Synthesis 2007, 327.
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Typical Procedure: Synthesis of Ethyl 4-Ethyl-6-hydroxy-3-methyl-2, methylthio)benzoate(4b) To a solution of 2b (0.190 g, 1.0 mmol) and 3b (0.549 g, 2.0 mmol) in CH2Cl2 (2 mL) was added TiCl4 (0.11 mL, 1.0 mmol) at -78°C under argon. The temperature of the reaction mixture was allowed to rise to 20°C during 14 h, and an aq HCl solution (10, 10 mL) was added. The organic layer was separated, and the aqueous layer was extracted with CH2Cl2 (3 x 10 mL, The combined organic layers were dried (Na2SO4, filtered, and concentrated in vacuo. After column chromatography (SiO2, heptane-EtOAc, 10:1, 4b was obtained as a colorless solid (227 mg, 89, mp 120-121°C; Rf, 0.39 (heptane-EtOAc, 3:1, 1H NMR (250 MHz, CDCl3, δ, 9.06 (s, 1 H, OH, 6.78 (s, 1 H, ArH, 4.43 q, 3J, 7.1 Hz, 2 H, OCH2
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3S (254.10): C, 61.39; H, 7.13. Found: C, 61.35; H, 7.27.
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CCDC-685823 contains all crystallographic details of this publication and is available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; or deposit@ccdc.cam.ac.uk.
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CCDC-685823 contains all crystallographic details of this publication and is available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; or deposit@ccdc.cam.ac.uk.
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