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[ CAS No. 75434-63-8 ] {[proInfo.proName]}

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Chemical Structure| 75434-63-8
Chemical Structure| 75434-63-8
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Product Details of [ 75434-63-8 ]

CAS No. :75434-63-8 MDL No. :MFCD16618477
Formula : C13H18O4S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 270.35 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 75434-63-8 ]

* 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 [ 75434-63-8 ]

[ 75434-63-8 ] Synthesis Path-Downstream   1~21

  • 1
  • [ 100-72-1 ]
  • [ 98-59-9 ]
  • [ 75434-63-8 ]
YieldReaction ConditionsOperation in experiment
80% The (tetrahydro-2H-pyran-2-yl)methanol (0.58 g, 5 mmol) and a stir bar were added to a 100 mL roundflask, then DCM (15 mL), Et3N (1.3 mL, 10 mmol, 2 eq) and DMAP (0.1 g, 0.75 mmol, 0.2 eq) wereadded. The mixture was stirred for 5 min and cooled to 0 C, then TsCl (1.05 g, 5.5 mmol, 1.1 eq) wasadded. After addition, the ice bath was removed and the mixture was kept stirring for 12 hours. The fullconsumption of the starting alcohol was confirmed by TLC. Water (20 mL) was added to the mixture andextracted with DCM (10 mL×3), the organic layer was combined and dried over Na2SO4 and concentratedunder vacuum. Column chromatography gave a white solid (1.1 g, 80%).1H NMR (CDCl3, 400 MHz): delta 7.79 (d, J = 8.3 Hz, 2H), 7.36-7.30 (m, 2H), 3.99-3.86 (m, 3H), 3.52 (dtd, J= 12.4, 5.2, 2.1 Hz, 1H), 3.36 (td, J = 11.3, 3.2 Hz, 1H), 2.43 (s, 3H), 1.87-1.78 (m, 1H), 1.59-1.38 (m,4H), 1.32-1.17 (m, 1H). 13C{1H} NMR (101 MHz, CDCl3) delta 144.67, 133.01, 129.73, 127.94, 74.87, 72.50,68.28, 27.55, 25.49, 22.70, 21.59. The NMR spectra are consistent with literature report5. CAS registryNo. 75434-63-8
68.7% With pyridine; at 0 - 20℃; Step 1 Preparation of (tetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate To a solution of (tetrahydro-2H-pyran-2-yl)methanol (2.32 g, 20.0 mmol) in pyridine (15 mL) was added a solution of TsCl (4.58 g, 24.0 mmol) in pyridine (10 mL) dropwise at 0 C. over 30 min. After stirred at room temperature for overnight, the reaction mixture was quenched with 10% aqueous citric acid solution, extracted with EtOAc (20 mL*3). The combined organic phases were dried over Na2SO4, filtered and concentrated to afford a residue, which was purified by silica column chromatography (petroleum ether:EtOAc=5:1) to give (tetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate (3.72 g, 68.7%) as a white solid.
With dmap; triethylamine; In dichloromethane; at 0℃; for 1h; General procedure: To a solution of alcohol (5.0 equiv) and N, N-dimethylaminopyridine(DMAP, 1.0 equiv) in CH2Cl2 was slowly added a solution ofp-toluenesulfonic chloride (TsCl) (5.5 equiv) in CH2Cl2 at 0 C, thenthe Et3N (10.0 equiv) was added. The reaction mixture was stirredat 0 C for 1 h, and then warmed to room temperature for another3 h. After diluted with water, the reaction mixture was extractedwith EtOAc.
  • 2
  • [ 75434-63-8 ]
  • [ 623-51-8 ]
  • [ 75434-65-0 ]
  • 4
  • [ 75434-63-8 ]
  • [ 151-50-8 ]
  • [ 75394-84-2 ]
  • 5
  • [ 75434-63-8 ]
  • (2E)-7-hydroxyhept-2-enenitrile [ No CAS ]
  • 8
  • [ 1187465-74-2 ]
  • [ 75434-63-8 ]
  • [ 1217422-73-5 ]
YieldReaction ConditionsOperation in experiment
With tetraethylammonium iodide; tetra(n-butyl)ammonium hydrogensulfate; tetra-(n-butyl)ammonium iodide; potassium carbonate; In toluene; for 14h;Reflux; A mixture of Example 7A (1.5 g, 4.32 mmol), Example 147A (2.34 g, 8.64 mmol), potassium carbonate (1.19 g, 8.64 mmol), tetrabutylammonium iodide (20 mg, 06 mmol), tetrabutylammonium hydrogen sulfate (20 mg, 0.05 mmol) and tetraethylammonium iodide (20 mg, 0.08 mmol) in toluene (50 mL) was heated at reflux for 14 hours. The mixture was washed with water, brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography to afford 480 mg of the title compound. MS (DCI/NH3) m/z 446 (M+H)+
  • 9
  • [ 75434-63-8 ]
  • [ 1431873-01-6 ]
  • [ 1431871-59-8 ]
  • [ 1431871-60-1 ]
YieldReaction ConditionsOperation in experiment
31% NaH (46 mg; 1.15 mmol) was added to a solution of intermediate 6 (208 mg; 0.57 mmol) in DMF (5 mL) under N2 at 10C. The solution was stirred at 10C for 30 minutes and 2H-Pyran-2-methanol tetrahydro-2-(4-methylbenzenesulfonate) (CAS 75434-63-8) (241 mg; 0.89 mmol) was added portion wise. The solution was allowed to slowly warm to room temperature, overnight, poured into ice and extracted with EtOAc. The organic layer was washed with brine, dried over MgS04, filtered off and the solvent was evaporated. The residue (0.69 g) was purified by chromatography over silica gel (Spherical Silica, deltamuetaiota, 150x30.0mm; mobile phase: gradient from0.2% NH4OH, 98% DCM, 2% MeOH to 0.8% NH4OH, 92% DCM, 8% MeOH). The product fractions were collected and the solvent was evaporated to give 2 fractions:Fraction 1 : 1 10 mg of a compound which was crystallized from acetone and Et20. The precipitate was filtered and dried to give 83 mg (31 %) of compound 129 . M.P.: 137C (Kofler).Fraction 2: 12 mg of an impure compound which was purified by achiral SFC (amino, deltamu iota, 150x21.2mm; mobile phase: gradient from 0.3% isopropylamine, 82% C02, 18% MeOH to 0.3% isopropylamine, 70% C02, 30% MeOH). The product fractions were collected and the solvent was evaporated to give 8 mg (3%) of compound 130 (94% of purity based on LC/MS).MP: 210C (kofler)
  • 10
  • [ 75434-63-8 ]
  • [ 1431873-03-8 ]
  • [ 1431871-65-6 ]
YieldReaction ConditionsOperation in experiment
9% NaH (87 mg; 2.19 mmol) was added under N2 at 10C to a solution of intermediate 7 (208 mg; 0.55 mmol) in DMF (5 ml_). The solution was stirred at 10C for 30 minutes. Tetrahydro-2H-pyran-2-ylmethyl 4-methylbenzenesulfonate (CAS 75434- 63-8) (443 mg; 1.64 mmol) was added portion wise and the solution was allowed to slowly warm to room temperature and stirred overnight. The reaction mixture was poured into ice and extracted with EtOAc. The organic layer was washed with brine, dried over MgS04, filtered and evaporated to dryness. The residue (0.25 g) was purified by chromatography over silica gel (Spherical Silica, 5pm, 150x30.0mm; mobile phase: gradient from 0% NH4OH, 0% MeOH, 100% DCM to 0.8% NH4OH, 92% DCM, 8% MeOH). The product fractions were collected and the solvent was evaporated to give 0.024 g (9%) of compound 139 . MP.: 94C (Kofler).
  • 11
  • [ 1119282-66-4 ]
  • [ 75434-63-8 ]
  • 1-(4-chloro-1-((tetrahydro-2H-pyran-2-yl)methyl)-1H-indol-3-yl)-2,2,2-trifluoroethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; Step 2 Preparation of 1-(4-chloro-1-((tetrahydro-2H-pyran-2-yl)methyl)-1H-indol-3-yl)-2,2,2-trifluoroethanone To a stirred solution of 1-(4-chloro-1H-indol-3-yl)-2,2,2-trifluoroethanone (2.0 g, 8.1 mmol) in DMF (20 mL) was added <strong>[75434-63-8](tetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate</strong> (2.6 g, 9.7 mmol), K2CO3 (3.4 g, 24.6 mmol) at room temperature. The resulting reaction mixture was stirred at 120 C. overnight, and then quenched with water and extracted with EtOAc (20 mL*3). The combined organic layers were washed with brine (20 mL*3), dried over Na2SO4, filtered and concentrated to give 1-(4-chloro-1-((tetrahydro-2H-pyran-2-yl)methyl)-1H-indol-3-yl)-2,2,2-trifluoroethanone (2.2 g, 81%) as red oil.
  • 12
  • [ 75434-63-8 ]
  • 4-chloro-1-((tetrahydro-2H-pyran-2-yl)methyl)-1H-indole-3-carboxylic acid [ No CAS ]
  • 13
  • [ 75434-63-8 ]
  • 4-chloro-N-((4,4-difluoro-1-hydroxycyclohexyl)methyl)-1-((tetrahydro-2H-pyran-2-yl)methyl)-1H-indole-3-carboxamide [ No CAS ]
  • 16
  • [ 75434-63-8 ]
  • diethyl 2-(2-iodoallyl)-2-((tetrahydro-2H-pyran-2-yl)methyl)malonate [ No CAS ]
  • 17
  • [ 75434-63-8 ]
  • diethyl 4-(iodomethyl)-6-oxaspiro[4.5]decane-2,2-dicarboxylate [ No CAS ]
  • 18
  • [ 75434-63-8 ]
  • (E)-4-(2-(((tetrahydro-2H-pyran-2-yl)methyl)sulfonyl)vinyl)benzene-1,2-diol [ No CAS ]
  • 19
  • [ 75434-63-8 ]
  • [ 68-11-1 ]
  • 2-(((tetrahydro-2H-pyran-2-yl)methyl)thio)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With sodium hydroxide; In methanol;Reflux; General procedure: The alkyl bromide (1.0 equiv) was added to a solution of mercaptoaceticacid (1.0 equiv) in methanol (10.0 mL) and the resultingsolution stirred. Then a solution of NaOH (2.0 equiv) in methanol(5.0 mL)was added slowly, and the final mixturewas stirred at roomtemperature or heated to reflux until absence of the alkyl bromide(checked by TLC). The reaction mixture was concentrated in vacuo,diluted with H2O, and neutralized with 1 N HCl. Then the obtainedreaction mixture was extracted with EtOAc. The combined organicfractions were washed with brine, dried with Na2SO4, and concentratedin vacuo. Purification of the crude residue by column chromatography(petroleum ether/EtOAc) afforded the title compound.
  • 20
  • bis(tetrabutylammonium) hexahydro-closo-hexaborate [ No CAS ]
  • [ 75434-63-8 ]
  • C6H17B6O(1-)*C16H36N(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; at 140℃; for 5h;Inert atmosphere; Sealed tube; Microwave irradiation; General procedure: In a nitrogen-filled glove box, the hexaboratedianion (0.6 or 0.8 mmol) and a stir bar were added to a 10 mL microwave tube. Dry CH3CN (0.5 mL) wasadded and stirred for 1 min until the dianion was fully dissolved. Pseudohalides (0.4 mmol) were addedvia 25 muL micro-syringe (used a spatula in the case of solids). The microwave tube was sealed andtransferred out of the glove box. The mixture was stirred in a microwave reactor at 140 C for 5 hours.The light orange solution was diluted with CH3CN, from 11B NMR the conversion could be determined.The solvent was removed in vacuo and the resulting oil was washed with Et2O (1 mL×3). Upon furtherdrying under vacuum, the crude product of the substituted cluster was dissolved in 2 mL of dry THF andtransferred to a 20 mL scintillation vial, pinacol (400 mg, 4 mmol) and a stir bar were added. Dry MgSO4(576 mg) was added and the mixture was stirred for 3 min and TCNQ (160 mg, 0.8 mmol) was added infour portions over 2 min at 0 C. The cold bath was then removed. Upon warming up to roomtemperature, the vial was heated at 40 C oil bath for 6 hours. The solvent was removed under reducedpressure and the residue was extracted with hexanes/ethyl acetate (10 mL, 4:1 v/v). The extract wasconcentrated and subjected to column separation to give the alkyl boronic ester products.
  • 21
  • [ 75434-63-8 ]
  • [ 221620-92-4 ]
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