Aluminium lithium hydride → 4-(3-Ethyl-2-hydroxyphenyl)-4-methyl-2-trifluoromethylpentane-1,2-diol

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Reaction Steps

Over-reduction of 10 g (23.51 mmol) of 4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester with lithium aluminum hydride for 14 days at reflux gave 570 mg (7.9%) of 4-(3-ethyl-2-hydroxyphenyl)-4-methyl-2-trifluoromethylpentane-1,2-diol which was methylated by methods analogous to those described in Example 8 and oxidized by methods analogous to those described in Example 1 to afford 4-(3-ethyl-2-methoxyphenyl)-1,1,1-trifluoro-4-methylpentan-2-one. The title compound was prepared by methods analogous to those described in Example 5, using 2-chloro-4-cyanobenzyl bromide.

Provenance & Evidence