Efficient, selective deprotection of aromatic acetates catalyzed by Amberlyst-15 or iodine

Tetrahedron Letters

Volumn 44, Issue 29, 2003, Pages 5465-5468

  Das, Biswanath ^a   Banerjee, Joydeep ^a   Ramu, R ^a   Pal, Rammohan ^a   Ravindranath, N ^a   Ramesh, C ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Amberlyst 15; Aromatic acetates; Chemoselectivity; Deprotection; Iodine

Indexed keywords

ACETIC ACID DERIVATIVE; ALIPHATIC COMPOUND; AMBERLYST 15; AROMATIC COMPOUND; CHEMICAL COMPOUND; IODINE; METHANOL; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; DEPROTECTION REACTION; DRUG SYNTHESIS; ROOM TEMPERATURE;

EID: 0037525480     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01298-X     Document Type: Article

References (13)

1. Kocienski P.G. Protecting Groups. 1994;Thieme, Stuttgart.
2. Greene T.W., Wuts P.G.M. Protecting Groups in Organic Synthesis. 2nd ed. 1995;Wiley, New York.
3. Kunitake T., Okahata Y., Sakamoto T. J. Am. Chem. Soc. 98:1976;7799.
4. Gonzalez A.G., Jorge Z.D., Dorta H.L., Rodriguez F.L. Tetrahedron Lett. 22:1981;335.
5. Tee O.S., Mazza C., LeZano-Hemmer R., Giorgi I.B. J. Org. Chem. 59:1994;7602.
6. Crampton M.R., Holt K.E., Perey J.M. J. Chem. Soc., Perkin Trans. 2. 1990;1701.
7. Beisselier V.L., Postal M., Dunach E. Tetrahedron Lett. 38:1997;2981.
8. Guo J., Huang W., Scanlan T.S. J. Am. Chem. Soc. 116:1994;6062.
9. Ramesh C., Mahender G., Ravindranath N., Das B. Tetrahedron. 59:2003;1049.
10. Bandgar B.P., Uppalla L.S., Sagar A.D., Sadavarte V.S. Tetrahedron Lett. 42:2001;1163.
11. Das B., Padma Rao S., Srinivas K.V.N.S., Yadav J.S. Phytochemistry. 33:1993;2529.
12. Murakami T., Matsushima A. J. Pharm. Soc. Jpn. 81:1961;1596.
13. 2 (100 mg) was stirred at room temperature. The progress of the reaction was monitored by TLC. After completion of the reaction, MeOH was removed under reduced pressure and the residue was extracted with EtOAc (3×10 ml). The extract was washed with a solution of sodium thiosulfate (3×10 ml) and subsequently with water (3×10 ml). The concentrated extract was subjected to column chromatography over silica gel to afford the parent phenol.