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Chemical Structure| 27088-84-2 Chemical Structure| 27088-84-2

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Chemical Structure| 27088-84-2

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Product Details of [ 27088-84-2 ]

CAS No. :27088-84-2
Formula : C10H9NOS
M.W : 191.25
SMILES Code : COC1=CC=C(C2=NC=CS2)C=C1
MDL No. :MFCD12033580

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Application In Synthesis of [ 27088-84-2 ]

* 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.

  • Upstream synthesis route of [ 27088-84-2 ]

[ 27088-84-2 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 27088-84-2 ]
  • [ 68-12-2 ]
  • [ 914348-82-6 ]
YieldReaction ConditionsOperation in experiment
78%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃;
Stage #2: at 0℃;
Stage #3: With acetic acid In tetrahydrofuran; hexane
(b)-1; Palladium acetate (0.82 g, 3.66 mmol), triphenylphosphine (4.80 g, 18.29 mmol), and a 2 M-sodium carbonate aqueous solution (183.0 mL, 366.0 mmol) were added to a solution of 2-bromothiazole (20.00 g, 121.94 mmol) and 4-methoxyphenylboric acid (25.94 g, 170.71 mmol) in DMF (400 mL). The obtained mixture was stirred at 100°C for 3 hours. Thereafter, water was added to the reaction solution, and it was then extracted with a mixture of ethyl acetate and toluene (1 : 1). The extract was washed with water and a saturated saline, and it was then dried over anhydrous sodium sulfate, followed by concentration. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain a thiazole compound (20.40 g, yield: 88percent) in the form of a yellow oily substance. Thereafter, n-butyl lithium (2.64 M hexane solution, 52.5 mL, 138.67 mmol) was added dropwise to a solution of the obtained thiazole compound (20.40 g, 106.67 mmol) in THF (500 mL) at -78°C. After stirring for 2 hours, DMF (16.4 mL, 213.33 mmol) was added dropwise to the reaction solution, and the reaction temperature was then raised to 0°C. The solution was stirred for 2 hours. Thereafter, acetic acid (7.9 mL, 138.67 mmol) was added dropwise to the reaction solution, and the solvent was then distilled away. The residue was dissolved in ethyl acetate, and water was then added to the solution and the two layers were separated. The water layer was extracted with ethyl acetate. The combined organic layer was washed with water and a saturated saline, and it was then dried over anhydrous sodium sulfate, followed by concentration. The residue was recrystallized from diisopropyl ether to obtain an aldehyde compound (18.31 g, yield: 78percent) in the form of a yellow powder.
References: [1] Patent: EP2308838, 2011, A1, . Location in patent: Page/Page column 69.
 

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