Lithiomethyl ethyl ether from chloromethyl ethyl ether via a DTBB-catalysed lithiation

被引：18
|
作者：
Guijarro, A [1 ]
Mancheno, B [1 ]
Ortiz, J [1 ]
Yus, M [1 ]
机构：
[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,E-03080 ALACANT,SPAIN
来源：
TETRAHEDRON | 1996年 / 52卷 / 05期
关键词：
D O I：
10.1016/0040-4020(95)00993-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of equimolecular amounts of chloromethyl ethyl ether (1) and a carbonyl compound [Bu(n)CHO, Bu(t)CHO, PhCHO, (Pr2CO)-C-i, Bu(2)(t)CO, (CH2)(4)CO, 2-cyclohexenone, PhCOMe] with an excess of lithium powder (1:7 molar ratio) and a catalytic amount of DTBB (5 mol %) in THF at 0 degrees C (Method A) leads, after hydrolysis, to the corresponding hydroxyethers 2. The reaction can be also carried out in a two-step process: tandem lithiation at -90 degrees C and reaction with the electrophile [Bu(n)CHO, (CH2)(4)CO, PhCOMe, PhMe(2)SiCl, CO2, PhCN, PhCONMe(2), CyNCO, PhN=CHPh] at -90 to -60 degrees C (Method B).
引用
收藏
页码：1643 / 1650
页数：8
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