Abstract
A simple and selective acetylation of primary alcohols in the presence of other reactive functionalities such as secondary alcohol, phenol, acetonide and amine is described using mild ethyl acetate as the acetyl-transfer agent and solid potassium carbonate as the catalyst.
References
1.
Green T.W.
, and
Wuts P.G.M.
, Protecting groups in organic synthesis , 4th edn. Wiley Interscience , New York , 2007 , pp. 223 –238 .
2.
Iqbal J.
, and
Srivastava R.R.
, J. Org. Chem. , 1992 , 57 , 2001 .
3.
Hofle G.
,
Steglich W.
, and
Vorbruggen H.
Angew Chem. Inter. Ed. Eng. , 1978 , 17 , 569 .
4.
Fischer A.
,
Hardman M.J.
,
Hartshorn M.P.
, and
Wright G.J.
Tetrahedron , 1969 , 25 , 5915 .
5.
Otera J.
, Chem. Rev. , 1993 , 93 , 1449 .
6.
Heravi M.M.
,
Bakhtiari K.
,
Javadi M.N.
, and
Oskooie H.
, Monats. Chem. , 2007 , 138 , 445 .
7.
Ranu B.C.
,
Dutta P.
, and
Sarkar A.
, J. Chem. Soc. Perkin Trans 1 , 2000 , 2223 .
8.
Hagiwara H.
,
Morohashi K.
,
Sakai H.
,
Suzuki T.
, and
Ando M.
, Tetrahedron , 1998 , 54 , 5845 .
9.
Ghiaci M.
,
Kalbasi R.J.
,
Mollahasani M.
, and
Aghaei H.
, Appl. Catal. A , 2007 , 320 , 35 .
10.
Singh R.
,
Kissling M.R.
,
Letellier M.-A.
, and
Steven Nolan P.
, J. Org. Chem. , 2004 , 69 , 209 .
11.
Ramalinga K.
,
Vijayalakshmi P.
, and
Kaimal T.N.B.
Tetrahedron Lett. , 2002 , 43 , 879 .
12.
John Bosco J. W.
,
Agrahari A.
, and
Anil Saikia K.
, Tetrahedron Lett. , 2006 , 47 , 4065 .
13.
Iwasaki T.
,
Maegawa Y.
,
Hayashi Y.
,
Ohshima T.
, and
Mashima K.
, Synlett , 2009 , 1659 .
14.
Dasgupta F.
,
George W.
,
Walter A.
, and
Szarek
. Carbohyd. Res. , 1983 , 114 , 153 .
15.
Liang Pi-Hui
,
Lu Yin-Jen
, and
Tang Ting-Hsuan
. Tetrahedron Lett. , 2010 , 51 , 6928 .
16.
Posner G. H.
, and
Oda M.
, Tetrahedron Lett. , 1981 , 22 , 5003 .