Preparation of cis- and trans-2,5-dimethoxytetrahydropyran and cis- and trans-2,5-dimethoxy-6-methyltetrahydropyran
1970 ◽
Vol 48
(15)
◽
pp. 2334-2340
◽
Keyword(s):
Hydroboration and subsequent oxidation of 2-methoxy-3,4-dihydro-2H-pyran gave a 1:2 mixture of cis- and trans-5-hydroxy-2-methoxytetrahydropyran (2). From the methylated product 4, trans-2,5-dimethoxytetrahydropyran could be obtained by gas–liquid chromatography. The cis-2,5-dimethoxy-tetrahydropyran (8) was obtained by conversion of 4 to 3-methoxy-3,4-dihydro-2H-pyran (6) which upon bromomethoxylation and subsequent reduction with palladium catalyst gave 8.Both cis- and trans-2,5-dimethoxy-6-methyltetrahydropyran (11) were obtained by hydroboration and oxidation of 2-methoxy-6-methyl-3,4-dihydro-2H-pyran (9) followed by methylation of the resulting product.
1974 ◽
Vol 92
(1)
◽
pp. 191-195
◽
Keyword(s):
1998 ◽
Vol 75
(8)
◽
pp. 977-985
◽
1985 ◽
Vol 50
(10)
◽
pp. 2275-2283
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Separation and Determination of cis- and trans- dl-Chrysanthemumic Acid by Gas Liquid Chromatography
1969 ◽
Vol 33
(7)
◽
pp. 1095-1096
◽
1966 ◽
Vol 44
(17)
◽
pp. 2015-2022
◽
1986 ◽
Vol 351
◽
pp. 512-517
◽
1976 ◽
Vol 17
(2)
◽
pp. 185-190
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