Factors affecting orthogonality in the deprotection of 2,4-di-protected aromatic ethers employing solid-supported acids

Tetrahedron

Volumn 65, Issue 22, 2009, Pages 4316-4325

  Tangdenpaisal, Kassrin ^a   Sualek, Supannee ^a   Ruchirawat, Somsak ^a,b,c   Ploypradith, Poonsakdi ^a,b  

^a Toxicology and Management of Chemicals   (Thailand)

^b Research and Innovation   (Thailand)

^c MAHIDOL UNIVERSITY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; CARBONYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DEPROTECTION REACTION; PHOTOCHEMICAL QUENCHING; PRIORITY JOURNAL; PROTON TRANSPORT;

EID: 65349143683     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.03.089     Document Type: Article

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25. For 3c, 52% and 35% yields of 2c were obtained using PTS-Si with MeOH (10 and 25 equiv, respectively). For 3d, 35% and 69% yields of 2d were obtained using Amberlyst-15 and PTS-Si in the presence of MeOH (10 equiv), respectively.
26. Anisole was employed as a cation scavenger for the PMB cation but resulted in even more complicated reaction mixtures without any remarkable difference for the decrease of the by-products from the FC-type C-alkylation.
27. Despite 0% yield of the desired mono-PMB-deprotected product 10 (see Table 3), the product mixture obtained from the reaction contained the mono-deprotected product, which was further alkylated via the FC-type process. It seems that the rates of the subsequent FC-type reactions of both mono- and di-deprotected are faster than the initial deprotection reaction.
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