AN EFFICIENT SYNTHETIC METHOD FOR BETA-CYCLOLAVANDULAL AND ITS CORRESPONDING ALCOHOL

Authors
ODA M ISOBE A HAYASHI M MIYATAKE R SHIMAO I KURODA S
Citation
M. Oda et al., AN EFFICIENT SYNTHETIC METHOD FOR BETA-CYCLOLAVANDULAL AND ITS CORRESPONDING ALCOHOL, Recueil des travaux chimiques des Pays-Bas, 115(10), 1996, pp. 438-440
Citations number
19
Categorie Soggetti
Chemistry
Journal title
Recueil des travaux chimiques des Pays-Bas → ACNP
ISSN journal
01650513
Volume
115
Issue
10
Year of publication
1996
Pages
438 - 440
Database
ISI
SICI code
0165-0513(1996)115:10<438:AESMFB>2.0.ZU;2-W
Abstract
3,3-Dimethylcyclohexanone (5) was efficiently converted to methyl beta -cyclolavandulate (6) in 74% yield in three steps, one of which includ ed the preparation of beta-methyl alpha,beta-unsaturated esters by cou pling lithium dimethylcuprate with enol phosphates of beta-oxo esters. Reduction of 6 with LiAlH4 gave beta-cyclolavandulol (2) in 94% yield and oxidation of 2 with pyridinium chlorochromate in the presence of molecular sieves afforded the title aldehyde quantitatively.