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Chemical Structure| 207990-68-9 Chemical Structure| 207990-68-9

Structure of 207990-68-9

Chemical Structure| 207990-68-9

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Product Details of [ 207990-68-9 ]

CAS No. :207990-68-9
Formula : C6(13C)H8OS
M.W : 141.20
SMILES Code : O=S([13CH3])C1=CC=CC=C1
MDL No. :MFCD15144852

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Application In Synthesis of [ 207990-68-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 207990-68-9 ]

[ 207990-68-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 34846-90-7 ]
  • [ 207990-68-9 ]
  • [ 1258074-97-3 ]
YieldReaction ConditionsOperation in experiment
86.9% [1-13C]-Methyl phenyl sulfoxide (2.5 g, 0.014 mol) and anhydrous THF (20 mL) were mixed in a 100 mL round bottom equipped with a magnetic stir bar and a rubber septum fitted to a nitrogen inlet. This mixture was stirred under a constant flow of nitrogen for a period of 10 minutes, after which it was then equilibrated at -78° C. in an ethanol dry ice bath. After about 10 minutes of equilibration, lithium diisopropylamide (17.7 mL, 1.8 eq) was added slowly for a period of 2 minutes. The resultant mixture was stirred for a period of 45 minutes to ensure complete anion formation. At that point, <strong>[34846-90-7]3-methoxy acrylic acid methyl ester</strong> (2.09 mL, 0.015 mol) was added neat to the reaction mixture still at -78° C. Initial 13CNMR in CDCl3 showed the formation of a new peak at 59 ppm and some starting material at 44 ppm (a ratio of 80percent to 20percent product starting material). The reaction mixture was allowed to go for an additional 3.0 hours and 13CNMR analysis of an aliquot in CDCl3 at that point showed 85percent conversion of starting material to product. After about 30 minutes of stirring, the reaction mixture was poured into a separatory funnel containing dichloromethane (75 mL) and deionised water (30 mL). This mixture was acidified to a pH of 2 and the organic layer was extracted (2.x.50 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and then concentrated using a rotary evaporator to afford 4.2 g of a red fluid. This crude product was purified by dry column chromatography (using 80percent EtoAc/20percent hexane as the eluent) to afford 2.74 g, 86.9percent of the titled compound light red oil, which immediately solidified on standing.The spectra data are as follows:1HNMR delta: 7.58-7.52 (m 5H); delta: 6.73-6.65 (m unresolved multiplet 1H); delta: 5.93-5.86 (ddd J 15.44, 6.98, 6.25, 1.1); delta: 3.99-3.31 (two sets of ddd J 149.28, 12.87, 7.72, 2H); delta: 3.72 (s 3H).13CNMR (75 MHz in CDCl3) delta: 138.60, 131.66, 129.43, 128.48, 59.04 and 55.13 (the carbonyl peak was not seen).
 

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