Tetrahedron p. 1643 - 1650 (1996)
Update date:2022-08-10
Topics:
Guijarro, Albert
Mancheno, Balbino
Ortiz, Javier
Yus, Miguel
The reaction of equimolar amounts of chloromethyl ethyl ether (1) and a carbonyl compound [Bu(n)CHO, Bu(t)CHO, PhCHO, Pr(i)2CO, Bu(t)2CO, (CH2)4CO, 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°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°C and reaction with the electrophile [Bu(n)CHO,(CH2)4CO, PhCOMe, PhMe2SiCl, CO2, PhCN, PhCONMe2, CyNCO, PhN=CHPh] at -90 to -60°C (Method B).
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