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Synlett 2005(10): 1527-1530  
DOI: 10.1055/s-2005-869838
LETTER
© Georg Thieme Verlag Stuttgart · New York

Mild and Chemoselective Deacetylation Method Using a Catalytic Amount of Acetyl Chloride in Methanol

Chang-Eun Yeom, So Young Lee, Young Jong Kim, B. Moon Kim*
School of Chemistry, College of Natural Sciences, Seoul National University, Seoul, 151-747, Korea
Fax: +82(2)8727505; e-Mail: kimbm@snu.ac.kr;
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Publication History

Received 30 March 2005
Publication Date:
12 May 2005 (online)

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Abstract

Efficient deacetylation of alcohol acetates under mild acidic conditions was accomplished with a catalytic amount of acetyl chloride in methanol. Acetates of various primary, secondary, aromatic and sugar alcohols were successfully deprotected. Highly chemoselective removal of acetyl groups in presence of ­other commonly employed esters was also achieved in excellent yields. The reactivity of this transesterification-mediated deacetyl­ation was found to be directly dependent upon the electronic and steric nature of the acetates.

Key words

acetyl chloride - acetate - catalytic - chemoselective - protecting group

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6

Representative Procedure.
To a magnetically stirred solution of acetic acid 3-phenyl-propyl ester (1.43 g, 8.00 mmol) in MeOH (8 mL), was added acetyl chloride (0.084 mL, 1.2 mmol) at r.t. The mixture was stirred for 3 h at r.t. and the reaction was quenched upon addition of sat. aq NaHCO3 solution (20 mL). The mixture was extracted with CH2Cl2 (2 × 20 mL). The combined organic extract was dried over anhyd MgSO4, filtered and concentrated. The resulting residue was purified through a pad (ca. 5 cm) of silica gel column to provide the desired alcohol (1.05 g, 96% yield).