A practical, efficient synthesis of 1,1-dioxo-hexahydro-1λ6-thiopyran-4-carbaldehyde

被引:16
作者
Bio, Matthew M. [1 ]
Hansen, Karl B. [1 ]
Gipson, John [1 ]
机构
[1] Amgen Inc, Chem Proc Res & Dev, Cambridge, MA 02139 USA
关键词
D O I
10.1021/op800108s
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A practical, efficient, and scalable procedure for the preparation of 1,1-dioxo-hexahydro-1 lambda(6)-thiopyran-4-carbaldehyde is reported. Synthesis of this aldehyde was complicated by high aqueous solubility of the product and the intermediates. The isolation and purification of the aldehyde was accomplished by conversion to the crystalline bisulfite adduct.
引用
收藏
页码:892 / 895
页数:4
相关论文
共 6 条
[1]   BRIEF PREPARATION OF THIAN-4-CARBOXYLIC ACID 1,1-DIOXIDE [J].
CARLON, E ;
DRAPER, RW ;
FRIARY, R .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1977, 9 (02) :94-96
[2]   SOME DERIVATIVES OF BICYCLO[2,2,1]HEPTANE-1-THIONIUM BROMIDE [J].
COCKBURN, WF ;
MCKAY, AF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (22) :5703-5706
[3]   A novel, nonaqueous method for regeneration of aldehydes from bisulfite adducts [J].
Kjell, DP ;
Slattery, BJ ;
Semo, HJ .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5722-5724
[4]   SULFUR TRIOXIDE IN OXIDATION OF ALCOHOLS BY DIMETHYL SULFOXIDE [J].
PARIKH, JR ;
DOERING, WVE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (21) :5505-&
[5]   Safe execution of a large-scale ozonolysis: Preparation of the bisulfite adduct of 2-hydroxyindan-2-carboxaldehyde and its utility in a reductive amination [J].
Ragan, JA ;
Ende, DJA ;
Brenek, SJ ;
Eisenbeis, SA ;
Singer, RA ;
Tickner, DL ;
Teixeira, JJ ;
Vanderplas, BC ;
Weston, N .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (02) :155-160
[6]   GENERAL ACID-CATALYZED BREAKDOWN OF KETONE BISULFITES [J].
YOUNG, PR ;
JENCKS, WP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (04) :1228-1235