Trifluoroacetic acid catalyzed tetrahydropyranylation of alcohols and phenols and direct conversion of THP ethers into acetates

被引:0
|
作者
Bodipati, Naganjaneyulu [1 ]
Palla, Srinivasa Rao [1 ]
Peddinti, Rama Krishna [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Roorkee 247667, Uttar Pradesh, India
关键词
Tetrahydropyranylation; trifluoroacetic acid; alcohols; phenols; THP ethers; acetates; SOLVENT-FREE TETRAHYDROPYRANYLATION; ONE-STEP CONVERSION; EFFICIENT CATALYST; HIGHLY EFFICIENT; CHEMOSELECTIVE TETRAHYDROPYRANYLATION; SYNTHETIC PROTOCOL; MILD; DEPROTECTION; TRIFLATE; CHLORIDE;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple procedure for tetrahydropyranylation of alcohols and phenols in dichloromethane and their depyranylation in methanol in the presence of trifluoroacetic acid at ambient temperature is described. This methodology is useful for substrates having functionalities such as ester, amide, nitro, aldehyde and olefinic bonds. Trifluoroacetic acid mediated direct conversion of tetrahydropyranyl ethers into their corresponding acetates is also described.
引用
收藏
页码:356 / 361
页数:6
相关论文
共 50 条
  • [31] Copper methanesulfonate-acetic acid as a novel catalytic system for tetrahydropyranylation-of alcohols and phenols
    Wang, Min
    Song, Zhi Guo
    Gong, Hong
    Jiang, Heng
    CHINESE CHEMICAL LETTERS, 2007, 18 (07) : 799 - 802
  • [32] Efficient and green tetrahydropyranylation and deprotection of alcohols and phenols by using activated carbon supported sulfuric acid
    Yang, Jin Hui
    Zhang, Xuan
    Liu, Wan Yi
    CHINESE CHEMICAL LETTERS, 2008, 19 (08) : 893 - 896
  • [33] Copper nitrate/acetic acid as an efficient synergistic catalytic system for the chemoselective tetrahydropyranylation of alcohols and phenols
    Min Wang
    Zhi-Guo Song
    Hong Gong
    Heng Jiang
    Monatshefte für Chemie - Chemical Monthly, 2009, 140 : 177 - 179
  • [34] Highly efficient tetrahydropyranylation of alcohols and phenols catalyzed by a new and reusable high-valent vanadium(IV) porphyrin
    Taghavi, S. Abdolmanaf
    Moghadam, Majid
    Mohammadpoor-Baltork, Iraj
    Tangestaninejad, Shahram
    Mirkhani, Valiollah
    Khosropour, Ahmad Reza
    COMPTES RENDUS CHIMIE, 2011, 14 (12) : 1095 - 1102
  • [35] Lithium triflate (LiOTf) catalyzed efficient and chemoselective tetrahydropyranylation of alcohols and phenols under mild and neutral reaction conditions
    Karimi, B
    Maleki, W
    TETRAHEDRON LETTERS, 2002, 43 (30) : 5353 - 5355
  • [36] ACID-CATALYZED ADDITION OF PHENOLS AND PHENYL ETHERS TO OLEIC ACID
    ROE, ET
    PARKER, WE
    SWERN, D
    JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1959, 36 (12) : 656 - 659
  • [37] Direct AlCl3-catalyzed transformation of benzyl THP ethers and allyl benzyl ethers
    Bui, Tien Tan
    Kim, Hee-Kwon
    SYNTHETIC COMMUNICATIONS, 2021, 51 (03) : 388 - 397
  • [38] Direct Conversion of TMS-ethers to THP-ethers Catalyzed by {[K.18-Crown-6]Br3}n
    Chehardoli, Gholamabbas
    Zolfigol, Mohammad Ali
    Derakhshanpanah, Fateme
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2019, 51 (02) : 192 - 197
  • [39] CYCLIZATION OF SELENIUM-COMPOUNDS DERIVED FROM TERPENIC ALCOHOLS OR ACETATES BY TRIFLUOROACETIC-ACID
    PERRIER, M
    ROUESSAC, F
    COMPTES RENDUS DE L ACADEMIE DES SCIENCES SERIE II, 1982, 295 (07): : 729 - 731
  • [40] Tetrahydropyranylation of alcohols and phenols using the synergistic catalyst system, copper(II) chloride-acetic acid
    Wang, Min
    Song, Zhi-Guo
    Jiang, Heng
    Gong, Hong
    MONATSHEFTE FUR CHEMIE, 2007, 138 (06): : 599 - 602