6-Methyl-6-hepten-2-one (3) on reaction with ethyl α-dimethylphosphonate/NaH gives a mixture of (E)-and (Z)-conjugated esters. The major (E)-isomer, (E)-ethyl-3,7-dimethyl-2,7-octadienoate (4), on reduction with LiAlH4 at room temperature furnishes (E)-3,7-dimethyl-2,7-octadien-l-ol (5) which on propionylation affords (E)-3,7-dimethyl-2,7-octadienyl propionate (1). Carbinol (5) is converted into its silyl ether (E)-2,6-dimethyl-8-t-butyldimethylsilyloxy-l,6-octadiene (6) witht-Bu(Me)2SiCl in CH2Cl2, which on hydroboronation-oxidation with 9-BBN/NaOH-H2O2 followed by disilylalion with (n-Bu)4N+ F− at room temperature, gives (E)-3,7-dimethyl-2-octen-l,8-diol (2).
Volume 134, 2022
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