Alkylation of 1-bromo-6-tetrahydropyranyloxyhexane with the dianion of 4-pentyn-1-ol yielded 11-tetrahydropyranyloxy-4-undecyn-1-ol (4) which upon catalytic hydrogenation and subsequent mesylation afforded (6). Li2CuCl4 catalysed the coupling of (6) with pentylmagnesium bromide gave 1-(tetrahydropyranyloxy)-7(Z)-hexadecene (8) which on depyranylation resulted in (Z)-7-hexadecen-1-ol (9). The alcohol (9) was then converted into the corresponding target compounds, (Z)-7-hexadecen-1-yl acetate (1) and (Z)-7-hexadecenal (2).
Volume 134, 2022
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