1,6-Hexanediol → Cholest-5-en-3alpha-yl 6-hydroxyhexyl Ether

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Reaction Steps

Using the procedure of Davis, J. Chem. Soc. 178-181 (1962), cholesterol tosylate and 1,6-hexanediol were condensed in refluxing dioxane to provide 52% yield of the title ether as colorless plates from hexane, m.p. 79.5°-81° C.; [α]D25 -28.1°±0.5° C.; IR 3500-3200 (OH), 1100 and 1080 cm-1 (ether); NMR (CDCL3): δ2.8-3.3 (br, 1H, H-1), 3.3-3.75 (2t,4H), 5.4 m, 1H).

Provenance & Evidence