Bulletin of the Chemical Society of Japan p. 3491 - 3496 (1995)
Update date:2022-08-16
Topics:
Sakamaki, Hiroshi
Kameda, Noriyuki
Iwadare, Tsukasa
Ichinohe, Yoshiyuki
The reaction of allylic alcohols in benzene-methanol (3:2) solvent in the presence of cis-dichlorobis(triphenylphosphine)platinum(II)-tin(II) chloride dihydrate complex catalyst afforded allylic methyl ethers.The structure of the obtained compounds was identified by direct comparison with authentic sample.Cholest-4-en-3α-ol, with a quasi-axial hydroxy group, gave a quantitative yield of 3α-methoxycholest-4-ene.On the other hand, cholest-4-en-3β-ol, with a guasi-equatorial hydroxy group, yielded 3β-methoxycholest-4-ene preferentially, but also yielded 3α-methoxycompound as a by-product, lowering the selectivity of the reaction.
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