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Chemical Structure| 1450657-28-9 Chemical Structure| 1450657-28-9

Structure of 1450657-28-9

Chemical Structure| 1450657-28-9

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Product Details of [ 1450657-28-9 ]

CAS No. :1450657-28-9
Formula : C12H16O5S
M.W : 272.32
SMILES Code : O=S(CC(C1=CC=C(OC)C(OCC)=C1)=O)(C)=O
MDL No. :MFCD28359366
InChI Key :NDPZMKPHRVBCLF-UHFFFAOYSA-N
Pubchem ID :71724545

Safety of [ 1450657-28-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 1450657-28-9 ]

* 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 [ 1450657-28-9 ]

[ 1450657-28-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1450657-28-9 ]
  • [ 608141-42-0 ]
YieldReaction ConditionsOperation in experiment
15% A mixture of 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanone (2 g, 7.34 mmol) and ammonium acetate (1.868 g, 24.24 mmol) in TFE (20 mL) was heated to reflux. The batch was slowly distilled, while a solution of NH4OAc (5 g) in TFE (100 mL) was charged at a rate sufficient to maintain a constant volume. When the addition was complete, the mixture was distilled until the total volume was 20 mL. Then, the mixture was cooled to 20 C., and transferred to a hydrogenation reaction vessel. To the mixture was charged bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate (0.034 g, 0.073 mmol) and (S)-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine (0.040 g, 0.073 mmol). The mixture was warmed to 50 C. and hydrogenated under 90 psig hydrogen gas for 18 h. Then, 50 mL water and 5 mL concentrated HCl were added, and the mixture was stirred at 20 C. for 1 h. Then, the mixture was extracted with EtOAc (2×50 mL), and the aqueous phase was made basic with aqueous 10N NaOH until pH10. The mixture was then extracted with EtOAc (2×50 mL), and the combined organic extracts were dried (MgSO4) and evaporated under vacuum to provide the product as a white solid (0.30 g, 15% yield); achiral HPLC (Hypersil BDS C8, 5.0 mum, 250×4.6 mm, 1.5 mL/min, 278 nm, 90/10 gradient to 80/20 0.1% aqueous TFA/MeOH over 10 min then gradient to 10/90 0.1% aqueous TFA/MeOH over the next 15 min): 8.85 (98.8%); chiral HPLC (Chiralpak AD-H 5.0 mum Daicel, 250×4.6 mm, 1.0 mL/min, 280 nm, 70:30:0.1 heptane-1-PrOH-diethylamine): 7.23 (3.98%), 8.17 (96.02%); 1H NMR (DMSO-d6) delta 1.32 (t, J=7.0 Hz, 3H), 2.08 (s, 2H), 2.96 (s, 3H), 3.23 (dd, J=3.6, 14.4 Hz, 1H), 3.41 (dd, J=9.4, 14.4 Hz, 1H), 3.73 (s, 3H), 4.02 (q, J=7.0 Hz, 2H), 4.26 (dd, J=3.7, 9.3 Hz, 1H), 6.89 (s, 2H), 7.02 (s, 1H); Anal. (C12H19NO4S)C, H, N. Calcd C, 52.73; H, 7.01; N, 5.12. Found C, 52.55; H, 7.26; N, 5.25.
  • 2
  • [ 1450657-28-9 ]
  • [ 253168-94-4 ]
YieldReaction ConditionsOperation in experiment
87.8% With palladium on activated charcoal; ammonium formate; In methanol; water; for 15h;Reflux; The formula IV compound 5mmol, ammonium formate 50mmol, methanol 40 ml, water 4 ml and a Pd/C 0.5g are successively added into a 100 ml single-port the bottle, reflux the reaction for 15h, filtering, methanol 10 ml wash the filter residue, the filtrate reducing pressure and evaporating solvent, adding water residue 25 ml and dichloromethane 25 ml, extracting the liquid, extract with methylene chloride (10 ml × 3), combined with the phase, salt water 20 ml washing, dry anhydrous sodium sulfate, filter, evaporate solvents filtrate under reduced pressure, the residue is EA10mL reflux washing 5 min, the cooling crystallization, 25 C stirring 0.5h, filtering, 40 C vacuum drying 5h, to obtain white solid 1.2g, yield 87.8%.
42.4% With ammonium formate; In methanol; water; for 20h;Reflux; 1.6 g of 1-(3-ethoxy-4-methoxy)phenyl-2-Methanesulfonyl ethanone3.15 g of ammonium formate, 40 mL of methanol, 4 mL of water were added to a 100 mL one-necked flask, and refluxed for 20 h. After the reaction was completed, the residue was washed with 10 mL of methanol, and the solvent was removed by distillation under reduced pressure, and then, 25 mL of water and 25 mL of dichloromethane were added to the filtrate, It was extracted three times with 30 mL of dichloromethane, and the organic phase was combined, washed with 20 mL of saturated brine, dried over anhydrous sodium sulfate and filtered. The filtrate was removed by distillation under reduced pressure. The residue was washed with 10 mL of ethyl acetate. After cooling and crystallization, stirred at room temperature for 0.5 h, filtered to give a white solid 1-(3-ethoxy-4-methoxy)phenyl-2-methanesulfonylethylamine 0.58g, yield 42.4%
 

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Technical Information

• Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • Grignard Reaction • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Nomenclature of Ethers • Nucleophilicity of Sulfur Compounds • Oxidation States of Sulfur Compounds • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Ethers • Preparation of Phosphorus and Sulfur Ylides • Prins Reaction • Ramberg-Bäcklund Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

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[ 1450657-28-9 ]

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