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[ CAS No. 203246-70-2 ] {[proInfo.proName]}

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Chemical Structure| 203246-70-2
Chemical Structure| 203246-70-2
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Product Details of [ 203246-70-2 ]

CAS No. :203246-70-2 MDL No. :
Formula : C7H12O2S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 160.23 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 203246-70-2 ]

* 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.

  • Downstream synthetic route of [ 203246-70-2 ]

[ 203246-70-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 134419-59-3 ]
  • [ 10387-40-3 ]
  • [ 203246-70-2 ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 77℃; Step 2: Synthesis of 2-Methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionic acid 30 g tetrahydro-2H-pyran-4-yl methansulfonate are dissolved in 270 ml degassed ethanol. 19.96 g potassium thioacetate are added and the reaction mixture is stirred at 77 C. for 12-18 h. Upon cooling to 20 C., the precipitate is filtered and rinsed twice with 90 ml degassed ethanol. 6.66 g sodium hydroxide solution (50%) are added to the filtrate, and the addition funnel is rinsed with 15 ml water. The reaction mixture is stirred at 25 C. for 1 h. 32.47 g 2-bromo-2-methyl-propionic acid ethyl ester ethyl are added to the mixture, and the addition funnel is rinsed with 30 ml ethanol. The stirring is continued for 1 h at 25 C. Afterwards, 450 ml solvent are removed by vacuum evaporation. 240 ml toluene are added and 120 ml solvent are distilled of 90 ml water are added and the phases are separated. To the organic layer subsequently 90 ml water, 2.75 g sodium tungstate dihydrate and 2.83 g tetrabutylammonium hydrogen sulfate are added. The reaction mixture is heated to 85 C. and 80.88 g hydrogen peroxide solution (35%) are added over a period of 1 h. The addition funnel is rinsed with 30 ml water. The stirring is continued for 1 h at 85 C. The reaction mixture is filtered and the phases are separated. The organic phase is subsequently washed with 12.66 g sodium metabisulfite dissolved in 114 ml water and again with 126 ml water. 19.98 g sodium hydroxide solution (50%) are added to the organic layer and the addition funnel is rinsed with 45 ml water. The reaction mixture is warmed to 50 C. for 1 h. The phases are separated. The water phase is cooled to 5 C. and acidified with 27.07 g HCl (37%). The stirring at 5 C. is continued for 1 h. The precipitate is filtered, rinsed with 37.5 ml water and dried at 50 C. 14.03 g of the product are obtained as a white solid. Yield: 35%. ES-MS: m/z 237 [M+H]; 1H NMR (400 MHz, DMSO-d6) delta ppm 1.53 (6H, s), 1.62-1.75 (2H, m), 1.85-1.92 (2H, m), 3.39 (2H, dt, 3JH,H=2.1 Hz, 3JH,H=11.7 Hz), 3.88-3.98 (3H, m), 13.63 (1H. s).
  • 2
  • [ 1768-64-5 ]
  • [ 10387-40-3 ]
  • [ 203246-70-2 ]
YieldReaction ConditionsOperation in experiment
75% In N,N-dimethyl-formamide; at 100℃; for 20h;Inert atmosphere; [00334] A solution of <strong>[1768-64-5]4-chlorotetrahydropyran</strong> (1.36 g, 1 1.28 mmol) and potassium ethanethioate (1.93 g, 16.92 mmol) in DMF (15.00 mL) was stirred at 100 C for 20 h at N2 atmosphere. It was monitored by LC-MS. After completed, it was diluted with ethyl acetate, washed with brine, the organic layer was dried over magnesium sulfate, filtered, and concentrated to yield the crude product. It was purified by SGC to yield S-tetrahydropyran-4-yl ethanethioate (1.36 g, 8.49 mmol, 75%) as a red oil.
In N,N-dimethyl-formamide; at 80℃; for 24h; A mixrue of <strong>[1768-64-5]4-chlorotetrahydro-2H-pyran</strong> (1 g, 8.29 mmol) and potassium ethanethioate (0.947 g, 8.29 mmol) in DMF (15 mL) was stirred at 80 C. for 24 h. The reaction mixture was cooled down and partitioned between hexane and cold 1N Na OH. The organic layer was washed with brine, dried (MgSO4), removed the solvent to afford S-tetrahydro-2H-pyran-4-yl ethanethioate as a pale brown oil. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.68 (2 H, m), 1.90 (2 H, m), 2.32 (3 H, s), 3.55 (2 H, m), 3.68 (1 H, m), 3.91 (2 H, dt, J=11.83, 3.90 Hz).
  • 3
  • [ 97986-34-0 ]
  • [ 10387-40-3 ]
  • [ 203246-70-2 ]
YieldReaction ConditionsOperation in experiment
86% sodium iodide; In N,N-dimethyl-formamide; at 20 - 50℃; To a solution of 300 g (1.175 mol) of Compound 24 in DMF (3 L) are added 268 g (2.35 mol) potassium thioacetate, followed by a catalytic amount of NaI (0.12 g, 10 mol %) at room temperature. After complete addition, the reaction is heated to 50 C. for 20 h. The reaction mixture is partitioned between TBME (3 L) and water (3 L), the aqueous layer is extracted with TBME (2 L), then saturated with NaCl and extracted again with TBME (2×2 L). The combined organic extracts are dried over Na2SO4, filtered and the solvent is removed under reduced pressure to afford 153 g of Compound 25. Yield: 81%; ES-MS: m/z 161 [M+H].
81% sodium iodide; In N,N-dimethyl-formamide; at 20 - 50℃; To a solution of 300 g (1.175 mol) of <strong>[97986-34-0]toluene-4-sulfonic acid tetrahydropyran-4-yl ester</strong> in DMF (3 L) are added 268 g (2.35 mol) potassium thioacetate, followed by a catalytic amount of NaI (0.12 g, 10 mol %) at room temperature. After complete addition, the reaction is heated to 50 C. for 20 h. The reaction mixture is partitioned between TBME (3 L) and water (3 L), the aqueous layer is extracted with TBME (2 L), then saturated with NaCl and extracted again with TBME (2*2 L). The combined organic extracts are dried over Na2SO4, filtered and the solvent is removed under reduced pressure to afford 153 g of thioacetic acid S-(tetrahydro-pyran-4-yl)ester. Yield: 81%; ES-MS: m/z 161 [M+H].
81% sodium iodide; In N,N-dimethyl-formamide; at 50℃; for 20h; Step 3: Synthesis of Thioacetic acid S-(tetrahydro-pyran-4-yl) ester To a solution of 300 g (1.175 mol) of toluene-4- sulfonic acid tetrahydro-pyran-4-yl ester in DMF (3 L) are added 268 g (2.35 mol) potassium thioacetate, followed by a catalytic amount of Nal (0.12 g, 10 mol%) at room temperature. After complete addition, the reaction is heated to 50 C for 20 h. The reaction mixture is partitioned between TBME (3 L) and water (3 L), the aqueous layer is extracted with TBME (2 L), then saturated with NaCl and extracted again with TBME (2 x 2 L). The combined organic extracts are dried over Na2S04, filtered and the solvent is removed under reduced pressure to afford 153 g of thioacetic acid S-(tetrahydro- pyran-4-yl) ester. Yield: 81%; ES-MS: m/z 161 [M+H]; 1H-NMR (250 MHz,CHLOROFORM-d) delta ppm 1.47 - 1.98 (4 H, m), 2.30 (3 H, s), 3.41 - 3.74 (3 H, m), 3.88 (2 H, dt, 7=11.76, 3.86 Hz)
81% With sodium iodide; In N,N-dimethyl-formamide; at 50℃; for 20h; Step 3: Synthesis of Compound A4 To a solution of 300 g (1.175 mol) of compound A3 in DMF (3 L) are added 268 g (2.35 mol) potassium thioacetate, followed by a catalytic amount of Nal (0.12 g, 10 mol%) at room temperature. After complete addition, the reaction is heated to 50 C for 20 h. The reaction mixture is partitioned between TBME (3 L) and water (3 L), the aqueous layer is extracted with TBME (2 L), then saturated with NaCl and extracted again with TBME (2 x 2 L). The combined organic extracts are dried over Na2S04, filtered and the solvent is removed under reduced pressure to afford 153 g of compound A4. Yield: 81%; ES-MS: m/z 161 [M+H].
81% sodium iodide; In N,N-dimethyl-formamide; at 20 - 50℃; for 20h; Step 3: Synthesis of compound D-4To a solution of 300 g (1.175 mol) of compound D-3 in DMF (3 L) are added 268 g (2.35 mol) potassium thioacetate, followed by a catalytic amount of Nal (0.12 g, 10 mol%) at room temperature. After complete addition, the reaction is heated to 50 C for 20 h. The reaction mixture is partitioned between TBME (3 L) and water (3 L), the aqueous layer is extracted with TBME (2 L), then saturated with NaCl and extracted again with TBME (2 x 2 L). The combined organic extracts are dried over Na2S04, filtered and the solvent is removed under reduced pressure to afford 153 g of compound D-4. Yield: 81%; ES-MS: m/z 161 [M+H]; *H-NMR (250 MHz, CHLOROFORM-d) delta ppm 1.47 - 1.98 (4 H, m), 2.30 (3 H, s), 3.41 - 3.74 (3 H, m), 3.88 (2 H, dt, 7=11.76, 3.86 Hz)
81% With sodium iodide; In N,N-dimethyl-formamide; at 50℃; for 20h; To 300 g (1.175 mol) of <strong>[97986-34-0]toluene-4-sulfonic acid tetrahydropyran-4-yl ester</strong> in DMF (3 L) are added 268 g (2.35 mol) potassium thioacetate, followed by a catalytic amount of NaI (0.12 g, 10 mol %) at RT. After complete addition, the reaction is heated to 50 C. for 20 h. The reaction mixture is partitioned between TBME (3 L) and water (3 L), the aq. layer is extracted with TBME (2 L), then saturated with NaCl and extracted again with TBME (2*2 L). The combined organic extracts are dried over Na2SO4, filtered and the solvent is removed under reduced pressure to afford 153 g of thioacetic acid S-(tetrahydro-pyran-4-yl) ester. Yield: 81%; ESI-MS: 161 [M+H]+
81% With sodium iodide; In N,N-dimethyl-formamide; at 50℃; for 20h; To 300 g (1 .175 mol) of <strong>[97986-34-0]toluene-4-sulfonic acid tetrahydropyran-4-yl ester</strong> in DMF (3 L) are added 268 g (2.35 mol) potassium thioacetate, followed by a catalytic amount of Nal (0.12 g, 10 mol%) at RT. After complete addition, the reaction is heated to 50 C for 20 h. The reactionmixture is partitioned between TBME (3 L) and water (3 L), the aq. layer is extracted with TBME (2 L), then saturated with NaCI and extracted again with TBME (2 x 2 L). The combined organic extracts are dried over Na2S04, filtered and the solvent is removed under reduced pressure to afford 153 g of thioacetic acid S-(tetrahydro-pyran-4-yl) ester. Yield: 81 %; ESI-MS: 161 [M+H]+
In N,N-dimethyl-formamide; at 50℃; for 12h; A mixture of potassium thioacetate (10.21 g; 87.62 mmol) and toluene-4-sulfonic acid tetrahydro-pyran-4-yl ester (11.23g; 43.81 mmol) in DMF (100 mL) was heated at 50 0C for 12 hours, cooled to room temperature, diluted with ether, washed with water, saturated NaHCO3 and brine and dried (MgSO4). Removal of the volatiles in vacuo provided a residue which was taken forward without additional purification.

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