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5-Methoxy-2H-chromen-2-one
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[ CAS No. 51559-36-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 51559-36-5
Chemical Structure| 51559-36-5
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Product Details of [ 51559-36-5 ]

CAS No. :51559-36-5 MDL No. :MFCD06797684
Formula : C10H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 176.17 Pubchem ID :-
Synonyms :

Safety of [ 51559-36-5 ]

Signal Word: Class:
Precautionary Statements: UN#:
Hazard Statements: Packing Group:

Application In Synthesis of [ 51559-36-5 ]

* 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 [ 51559-36-5 ]

[ 51559-36-5 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 51559-36-5 ]
  • [ 82243-02-5 ]
Reference： [1]Bulletin de la Classe des Sciences, Academie Royale de Belgique,1953,vol. <5> 39,p. 1064,1074
[2]Monatshefte fur Chemie,1944,vol. 75,p. 14,22
  • 2
  • [ 150-19-6 ]
  • [ 471-25-0 ]
  • [ 531-59-9 ]
  • [ 51559-36-5 ]
YieldReaction ConditionsOperation in experiment
47%; 11% With trifluoroacetic acid; In chlorobenzene; at 100℃; for 1h;Inert atmosphere; General procedure: A mixture of Phenol derivatives (1) (1.0 mmol), trifluoromethanesulfonic acid (1.0 mmol) and propiolic acid (2a) (0.5 mmol) in PhCl (3.0 mL) was stirred at 100 C for 1 h. After completion of reaction as indicated by TLC, the reaction mixture was poured into H2O, neutralized with NaHCO3 solution and extracted CH2Cl2. The organic layer was washed with 2M NaOH, dried over anhydrous MgSO4. The solvent was removed in vaccum, and the products were purified by silica gel columnchromatography (EtOAc-Hex) to give the desired product 3.
47%; 11% With trifluorormethanesulfonic acid; In chlorobenzene; at 100℃; for 1h; General procedure: Cresol instead of phenol, and the reaction time was 1 hour, the title compound was synthesized in the same manner as in Example 1. White solid (59 mg, 74%)
Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 3600 - 3603
[2]Patent: KR101656876,2016,B1 .Location in patent: Paragraph 0119; 0120
[3]Tetrahedron,2006,vol. 62,p. 6918 - 6925
[4]Tetrahedron,2006,vol. 62,p. 6918 - 6925
[5]Synthesis,2004,p. 1466 - 1470
[6]Synthesis,2011,p. 1283 - 1289
  • 3
  • [ 51559-36-5 ]
  • [ 133407-38-2 ]
  • [ 208993-91-3 ]
  • C20H25NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / tetrahydrofuran / 15 °C / Inert atmosphere; Large scale 1.2: Inert atmosphere; Large scale 2.1: lithium borohydride / tetrahydrofuran / -15 °C / Inert atmosphere; Large scale 2.2: 3 h / 65 °C / Inert atmosphere; Large scale
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / tetrahydrofuran / 8 - 10 °C / Inert atmosphere; Large scale 2.1: lithium borohydride / tetrahydrofuran / -15 °C / Inert atmosphere; Large scale 2.2: 3 h / 65 °C / Inert atmosphere; Large scale
Reference： [1]Haight, Anthony R.; Bailey, Anne E.; Baker, William S.; Cain, Michael H.; Copp, Richard R.; Demattei, John A.; Ford, Kelley L.; Henry, Rodger F.; Hsu, Margaret C.; Keyes, Robert F.; King, Steven A.; McLaughlin, Maureen A.; Melcher, Laura M.; Nadler, William R.; Oliver, Patricia A.; Parekh, Shyamal I.; Patel, Hemant H.; Seif, Louis S.; Staeger, Mike A.; Wayne, Gregory S.; Wittenberger, Steven J.; Zhang, Weijiang [Organic Process Research and Development, 2004, vol. 8, # 6, p. 897 - 902]
[2]Haight, Anthony R.; Bailey, Anne E.; Baker, William S.; Cain, Michael H.; Copp, Richard R.; Demattei, John A.; Ford, Kelley L.; Henry, Rodger F.; Hsu, Margaret C.; Keyes, Robert F.; King, Steven A.; McLaughlin, Maureen A.; Melcher, Laura M.; Nadler, William R.; Oliver, Patricia A.; Parekh, Shyamal I.; Patel, Hemant H.; Seif, Louis S.; Staeger, Mike A.; Wayne, Gregory S.; Wittenberger, Steven J.; Zhang, Weijiang [Organic Process Research and Development, 2004, vol. 8, # 6, p. 897 - 902]
  • 4
  • [ 51559-36-5 ]
  • [ 133407-38-2 ]
  • C20H21NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
98 % de Stage #1: 5-methoxycoumarin; (R)-N-(1-phenylethyl)-N-(methoxymethyl)-N-(trimethylsilylmethyl)amine With trifluoroacetic acid In tetrahydrofuran at 15℃; Inert atmosphere; Large scale; Stage #2: In n-heptane; ethyl acetate Inert atmosphere; Large scale; diastereoselective reaction;
Reference： [1]Haight, Anthony R.; Bailey, Anne E.; Baker, William S.; Cain, Michael H.; Copp, Richard R.; Demattei, John A.; Ford, Kelley L.; Henry, Rodger F.; Hsu, Margaret C.; Keyes, Robert F.; King, Steven A.; McLaughlin, Maureen A.; Melcher, Laura M.; Nadler, William R.; Oliver, Patricia A.; Parekh, Shyamal I.; Patel, Hemant H.; Seif, Louis S.; Staeger, Mike A.; Wayne, Gregory S.; Wittenberger, Steven J.; Zhang, Weijiang [Organic Process Research and Development, 2004, vol. 8, # 6, p. 897 - 902]
  • 5
  • [ 51559-36-5 ]
  • [ 133407-38-2 ]
  • C20H21NO3 [ No CAS ]
  • C20H21NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
25.926 % de With trifluoroacetic acid In tetrahydrofuran at 8 - 10℃; Inert atmosphere; Large scale; Overall yield = 45.8 %; Overall yield = 18.9 kg; diastereoselective reaction;
Reference： [1]Haight, Anthony R.; Bailey, Anne E.; Baker, William S.; Cain, Michael H.; Copp, Richard R.; Demattei, John A.; Ford, Kelley L.; Henry, Rodger F.; Hsu, Margaret C.; Keyes, Robert F.; King, Steven A.; McLaughlin, Maureen A.; Melcher, Laura M.; Nadler, William R.; Oliver, Patricia A.; Parekh, Shyamal I.; Patel, Hemant H.; Seif, Louis S.; Staeger, Mike A.; Wayne, Gregory S.; Wittenberger, Steven J.; Zhang, Weijiang [Organic Process Research and Development, 2004, vol. 8, # 6, p. 897 - 902]

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