Acetylation and formylation of alcohols with triphenylphosphine and carbon tetrabromide in ethyl acetate or ethyl formate

被引:59
作者
Hagiwara, H
Morohashi, K
Sakai, H
Suzuki, T
Ando, M
机构
[1] Niigata Univ, Grad Sch Sci & Technol, Niigata 95021, Japan
[2] Niigata Univ, Fac Engn, Niigata 95021, Japan
关键词
D O I
10.1016/S0040-4020(98)00255-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alcohols were acetylated or formylated with triphenylphosphine and carbon tetrabromide in ethyl acetate or ethyl (or methyl) formate at room temperature. THP or TBDMS ether of primary alcohol got converted into formate or acetate under the experimental conditions employed in one pot operation. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5845 / 5852
页数:8
相关论文
共 24 条
[1]  
BARRETT AGM, 1997, J CHEM SOC CHEM COMM, P351
[2]   ENZYMATIC ESTERIFICATION AND DE-ESTERIFICATION OF CARBOHYDRATES - SYNTHESIS OF A NATURALLY-OCCURRING RHAMNOPYRANOSIDE OF P-HYDROXYBENZALDEHYDE AND A SYSTEMATIC INVESTIGATION OF LIPASE-CATALYZED ACYLATION OF SELECTED ARYLPYRANOSIDES [J].
BASHIR, NB ;
PHYTHIAN, SJ ;
REASON, AJ ;
ROBERTS, SM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (18) :2203-2222
[3]  
CALZADA JG, 1988, ORG SYNTH, V6, P634
[4]  
GREENE TW, 1991, PROTECTIVE GROUPS OR
[5]  
HAGIWAR H, IN PRESS SYNTH COMMU
[6]   TOTAL SYNTHESIS OF (+)-DIHYDROCOMPACTIN [J].
HAGIWARA, H ;
KONNO, M ;
NAKANO, T ;
UDA, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (17) :2417-2430
[7]   Facile preparation of thiocarbonylimidazolide by organic solid state reaction [J].
Hagiwara, H ;
Ohtsubo, S ;
Kato, M .
TETRAHEDRON, 1997, 53 (07) :2415-2420
[8]   TOTAL SYNTHESIS OF (+)-COMPACTIN BY A DOUBLE MICHAEL PROTOCOL [J].
HAGIWARA, H ;
NAKANO, T ;
KONNO, M ;
UDA, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (07) :777-783
[9]   AN EXTREMELY SIMPLE, CONVENIENT, AND SELECTIVE METHOD FOR ACETYLATING PRIMARY ALCOHOLS IN THE PRESENCE OF SECONDARY ALCOHOLS [J].
ISHIHARA, K ;
KURIHARA, H ;
YAMAMOTO, H .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3791-3793
[10]   SCANDIUM TRIFLUOROMETHANESULFONATE AS AN EXTREMELY ACTIVE ACYLATION CATALYST [J].
ISHIHARA, K ;
KUBOTA, M ;
KURIHARA, H ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (15) :4413-4414