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[ CAS No. 959748-73-3 ]

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2D
Chemical Structure| 959748-73-3
Chemical Structure| 959748-73-3
Structure of 959748-73-3 *Storage: {[proInfo.prStorage]}

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Product Details of [ 959748-73-3 ]

CAS No. :959748-73-3MDL No. :MFCD23378508
Formula : C14H20O4S Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :284.37Pubchem ID :-
Synonyms :

Computed Properties of [ 959748-73-3 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

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Application In Synthesis of [ 959748-73-3 ]

  • Downstream synthetic route of [ 959748-73-3 ]

[ 959748-73-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 4677-18-3 ]
  • [ 98-59-9 ]
  • [ 959748-73-3 ]
YieldReaction ConditionsOperation in experiment
53% In pyridine; at 20℃; for 5h; To a solution of 1.63 g (12.5 mmol) of Compound 18 in pyridine (15 mL) are added 3.58 g (18.8 mmol) of p-toluenesulfonylchloride. The reaction is stirred at room temperature for 5 h. The reaction mixture is concentrated under reduced pressure. The residue is dissolved 2M aqueous HCl solution (20 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts are dried over Na2SO4, filtered and the solvent is removed to give 1.9 g of Compound 19 as off-white crystalline solid. Yield: 53%; ES-MS: m/z 285 [M+H]; 1H-NMR (500 MHz, CHLOROFORM-d) delta ppm 1.17-1.29 (2H, m), 1.45-1.52 (2H, m), 1.57-1.67 (3H, m), 2.46 (3H, s), 3.32 (2H, td, J=11.78, 1.93 Hz), 3.91 (2H, dd, J=11.28, 4.13 Hz), 4.08 (2H, t, J=6.14 Hz), 7.36 (2H, d, J=8.07 Hz), 7.80 (2H, d, J=8.44 Hz).
53% With pyridine; at 20℃; for 5h; Step 2: Synthesis of Compound D3To a solution of 1.63 g (12.5 mmol) of compound D2 in pyridine (15 mL) are added 3.58 g (18.8 mmol) of p-toluenesulfonylchloride. The reaction is stirred at room temperature for 5 h. The reaction mixture is concentrated under reduced pressure. The residue is dissolved 2M aqueous HC1 solution (20 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organic extracts are dried over Na2S04, filtered and the solvent is removed to give 1.9 g of compound D3 as off-white crystalline solid. Yield: 53%; ES-MS: m/z 285 [M+H]; 1H-NMR (500 MHz, CHLOROFORM-d) delta ppm 1.17 - 1.29 (2 H, m), 1.45 - 1.52 (2 H, m), 1.57 - 1.67 (3 H, m), 2.46 (3 H, s), 3.32 (2 H, td, 7=11.78, 1.93 Hz), 3.91 (2 H, dd, 7=11.28, 4.13 Hz), 4.08 (2 H, t, 7=6.14 Hz), 7.36 (2 H, d, 7=8.07 Hz), 7.80 (2 H, d, 7=8.44 Hz)
With pyridine; In dichloromethane; at 20℃; for 3.25h; Example 220A 2-(tetrahydro-2H-pyran-4-yl)ethyl4-methylbenzenesulfonate To a solution of <strong>[4677-18-3]2-(tetrahydropyran-4-yl)-ethanol</strong> (1.5 g, 11.5 mmol) in 10 mL of CH2Cl2 and 7 mL of pyridine was added p-toluenesulfonyl chloride (2.4 g, 12.7 mmol) portion wise over 15 minutes. The mixture stirred at ambient temperature for 3 hours and was quenched with 10 mL of saturated, aqueous NaHCO3. The layers were separated and the aqueous layer was extracted with three 5 mL of portions of CH2Cl2. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via column chromatography (SiO2, 70% hexanes in ethyl acetate) afforded the title compound. MS (DCI/NH3) m/z 302 (M+NH4)+.
With pyridine; In dichloromethane; at 20℃; for 72h; p-Toluenesulfonyl chloride (2.998 g, 16 mmol) was added to a solution of 2-(tetrahydro-pyran-4-yl)ethanol (CASRN 4677-18-3, 1.706 g, 13 mmol), pyridine (1.16 mL, 14 mmol) and DCM (10 mL). The resulting mixture was stirred at RT for 72 h. The solution was partitioned between EtOAc and saturated NH4Cl. The aqueous layer was back extracted twice with EtOAc. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo to afford 70 as colorless oil.
With pyridine; In dichloromethane; at 20℃; for 3.25h; To a solution of <strong>[4677-18-3]2-(tetrahydropyran-4-yl)-ethanol</strong> (1.5 g, 1 1.5 mmol) in 10 mL OfCH2Cl2 and 7 mL of pyridine was added p- toluenesulfonyl chloride (2.4 g, 12.7 mmol) portion wise over 15 <n="133"/>minutes. The mixture stirred at ambient temperature for 3 hours and was quenched with 10 mL of saturated, aqueous NaHCCh. The layers were separated and the aqueous layer was extracted with three 5 mL of portions OfCH2Cl2. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via column chromatography (SiO2, 70% hexanes in ethyl acetate) afforded the title compound. MS (DCI/NH3) m/z 302 (M+NH4)+
840 mg With triethylamine; In dichloromethane; at 0 - 20℃; 629 mul (4.47 mmol) of triethylamine and 813 mg (4.10 mmol) of p-toluenesulfonyl chloride are added to a solution of 500 mg (3.73 mmol) of <strong>[4677-18-3]2-(tetrahydropyran-4-yl)ethanol</strong> in 15 mL of DCM previously cooled to 0C. The reaction mixture is stirred at room temperature overnight. The solution is taken up in DCM, washed with aqueous NaHCO3 solution, dried over magnesium sulfate and then evaporated to dryness. The residue is purified by chromatography on silica gel (eluent: 20/80 EtOAc/heptane) to give 840 mg of 2-(tetrahydro-2H-pyran-4-yl)ethyl 4-methylbenzenesulfonate, corresponding to the following characteristics: 1H NMR (300 MHz, delta in ppm, CDCl3): 1.15-1.32 (m, 2H), 1 .45-1.74 (m, 5H), 2.47 (s, 3H), 3.33 (td, 2H), 3.88-3.96 (m, 2H), 4.09 (t, 2H), 7.37 (d, 2H), 7.82 (d, 2H).
840 mg With triethylamine; In dichloromethane; at 0 - 20℃; 629 muL (4.47 mmol) of triethylamine and 813 mg (4.10 mmol) of p-toluenesulfonyl chloride are added to a solution of 500 mg (3.73 mmol) of <strong>[4677-18-3]2-(tetrahydropyran-4-yl)ethanol</strong> in 15 mL of DCM previously cooled to 0 C. The reaction mixture is stirred at room temperature overnight. The solution is taken up in DCM, washed with aqueous NaHCO3 solution, dried over magnesium sulfate and then evaporated to dryness. The residue is purified by chromatography on silica gel (eluent: 20/80 EtOAc/heptane) to give 840 mg of 2-(tetrahydro-2H-pyran-4-yl)ethyl 4-methylbenzenesulfonate, corresponding to the following characteristics: 1H NMR (300 MHz, delta in ppm, CDCl3): 1.15-1.32 (m, 2H), 1.45-1.74 (m, 5H), 2.47 (s, 3H), 3.33 (td, 2H), 3.88-3.96 (m, 2H), 4.09 (t, 2H), 7.37 (d, 2H), 7.82 (d, 2H).
With pyridine; at 20℃;Cooling with ice; To an ice-cold solution of <strong>[4677-18-3]2-(tetrahydro-2H-pyran-4-yl)ethanol</strong> (1.00 g) in pyridine (6.5 mL) was added p-toluenesulfonyl chloride (1.5 g), followed by stirring at the same temperature for 30 minutes, and at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and then diluted aqueous hydrochloric acid (20 mL) was added to the residue, followed by twice extractions with ethyl acetate (20 mL). The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=80/20-50/50) to obtain p-toluenesulfonic acid 2-(tetrahydro-2H-pyran-4-yl)ethyl ester (450 mg).

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