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Chemical Structure| 17689-66-6 Chemical Structure| 17689-66-6

Structure of 17689-66-6

Chemical Structure| 17689-66-6

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Product Details of [ 17689-66-6 ]

CAS No. :17689-66-6
Formula : C12H18O4S
M.W : 258.33
SMILES Code : O=S(C1=CC=C(C)C=C1)(OCCC(C)(O)C)=O
MDL No. :MFCD26384653
InChI Key :GGLYIKZLOPXYOV-UHFFFAOYSA-N
Pubchem ID :14001295

Safety of [ 17689-66-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H311-H331-H341
Precautionary Statements:P201-P202-P261-P264-P270-P271-P280-P302+P352-P304+P340-P308+P313-P310-P330-P361-P403+P233-P405-P501
Class:6.1
UN#:2811
Packing Group:

Application In Synthesis of [ 17689-66-6 ]

* 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 [ 17689-66-6 ]

[ 17689-66-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 164513-38-6 ]
  • [ 17689-66-6 ]
  • [ 955930-01-5 ]
YieldReaction ConditionsOperation in experiment
Production Example 35 In an atmosphere of nitrogen, sodium hydride was added under ice-cooling to a mixture of <strong>[164513-38-6]5-bromo-4-methylpyridin-2-ol</strong> and DMF, followed by stirring at room temperature for 1 hour. Then, 3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate was added thereto, followed by stirring at 40C for 14 hours to obtain 4-[(5-bromo-4-methylpyridin-2-yl)oxy]2-methylbutan-2-ol and 5-bromo-1-(3-hydroxy-3-methylbutyl)-4-methylpyridin-2(1H)-one.
<Step 2> Synthesis of 4-(5-bromo-4-methylpyridin-2-yloxy)-2-methylbutan-2-ol To a suspension of sodium hydride (to which about 40% of a mineral oil was added, 0.23 g) in N,N-dimethylformamide (10 mL), <strong>[164513-38-6]5-bromo-2-hydroxy-4-methylpyridine</strong> (1.00 g) was added under ice-cooling and the resultant reaction mixture was stirred for 30 minutes. To the reaction mixture, 3-hydroxy-3-methylbutyl 4-methylbenzene sulfonate (1.51 g) was added and the resultant reaction mixture was stirred at 60 C. for 4 hours. To the reaction mixture, a aqueous solution of saturated ammonium chloride was added and the resultant reaction mixture was extracted with ethyl acetate. The organic phase was washed with saturated saline and was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluate; n-hexane:ethyl acetate=50:50 to 33:67) to obtain the subject compound (0.92 g) as a light yellow oil.
<Step 2> Synthesis of 4-(5-bromo-4-methylpyridin-2-yloxy)-2-methylbutan-2-ol To a suspension of sodium hydride (to which about 40% of a mineral oil was added, 0.23 g) in N,N-dimethylformamide (10 mL), <strong>[164513-38-6]5-bromo-2-hydroxy-4-methylpyridine</strong> (1.00 g) was added under ice-cooling and the resultant reaction mixture was stirred for 30 minutes. To the reaction mixture, 3-hydroxy-3-methylbutyl 4-methylbenzene sulfonate (1.51 g) was added and the resultant reaction mixture was stirred at 60 C. for 4 hours. To the reaction mixture, a saturated ammonium chloride aqueous solution was added and the resultant reaction mixture was extracted with ethyl acetate. The organic phase was washed with a saturated saline and was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluate; n-hexane:ethyl acetate=50:50 to 33:67) to obtain the subject compound (0.92 g) as a pale yellow oil.
  • 2
  • [ 17689-66-6 ]
  • [ 35979-69-2 ]
YieldReaction ConditionsOperation in experiment
89% With lithium bromide; In tetrahydrofuran; at 20℃;Inert atmosphere; Step 2. Preparation of 4-bromo-2-methylbutan-2-ol To a solution of 3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate (400 mg, 1.548 mmol) in THF (15 mL) at room temperature was added lithium bromide (403 mg, 4.65 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was transferred to a separatory funnel containing saturated aqueous aHC03 solution (10 mL) and water (10 mL). The aqueous layer was extracted with ether (3 x 20 mL). The combined organic layers were washed with brine (10 mL), dried over MgS04, filtered, and concentrated. The product was purified by column chromatography on silica gel (20%→ 40% ethyl acetate in hexanes; 80 g column) to afford 4-bromo-2-methylbutan-2- ol (231 mg, 1.383 mmol, 89% yield) as a colorless oil: NMR (500MHz, CHLOROFORM-d) δ 3.55 - 3.49 (m, 2H), 2.15 - 2.09 (m, 2H), 1.28 (s, 6H).
85.28% With sodium bromide; In N,N-dimethyl-formamide; acetone; for 6h;Inert atmosphere; Reflux; Under the protection of nitrogen, add 0.05mol 3-methyl-3-butanol-1-p-toluenesulfonate, 0.08mol sodium bromide and 20mL acetone to the 500mL reaction flask, heat to reflux with magnetic stirring, then add 0.05mol DMF (moisture 2.5%), continue to reflux for 7.0h;After the reaction, the acetone was recovered under reduced pressure, 60 mL of water was added to dissolve the solid, and extracted with dichloromethane three times. The organic phases were combined, the dichloromethane was recovered, and the concentrate was purified under reduced pressure. The GC content is 86.86%, and the yield calculated from 3-methyl-3-butanol-1-p-toluenesulfonate is 85.28%.
77.4% With lithium bromide; In tetrahydrofuran; at 20℃; for 10h; (6) Weigh 3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate (2.6g, 10.1mmol) into dry tetrahydrofuran (20ml), Lithium bromide (2.62g, 30.3mmol) was added and reacted at room temperature for 10 h. Purification by column chromatography gave a yellow oil (1.3 g, 77.4% yield), which was 4-bromo-2-methylbutan-2-ol.
 

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