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).

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页码：1643 / 1650

页数：8

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