Journal of Organic Chemistry p. 5063 - 5066 (1993)
Update date:2022-08-28
Topics:
Doolittle, Robert E.
Patrick, Delrea G.
Heath, Robert H.
Reduction of the THP, ethyl, tert-butyl and tert-butyldimethylsilyl (TBDMS) ethers of 3-decyn-1-ol with sodium in ammonia/THF results in extensive hydrogenolysis of the carbon-oxygen bond and concomitant bond migration, producing a mixture of 2- and 3-decenes and a very low yield of the desired (E)-homoallylic ether.Reduction in the presence of 2-methyl-2-propanol led to excellent yields of the desired (E)-3-decenol ethers.The 4- and 5-decyn-1-ol ethers were reduced normally to the (E)-decen-1-ol ethers except in the case of the TBDMS ethers which were cleaved to the (E)-alcohols under some of the reaction conditions.
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