Diethyl Ether → (7-Isopropylidene-2,5-dimethyl-bicyclo[2.2.1]hept-5-en-2-yl)-methanol

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Reaction Steps

A mixture of 5-isopropylidene-2-methyl-cyclopenta-1,3-diene (26.4 g, 0.22 mol) and methacroleine (29.4 g, 0.42 mol) were stirred for 2 days at room temperature. The mixture was diluted with diethyl ether (50 ml) and added dropwise at 0° C. to a suspension of LiAlH4 (6.25 g, 0.16 mol) in ether (100 ml). After having been stirred for 1 h at room temperature, the mixture was dropwise quenched successively with water (6 ml), NaOH (15%, 6 ml) and water (6 ml). The mixture was filtered, concentrated in vacuo and the residue was purified by chromatography on silica gel (hexane:MTBE=9:1) to yield 21.6 g of a colorless oil.

Provenance & Evidence