Preparation of cis- and trans-2,5-dimethoxytetrahydropyran and cis- and trans-2,5-dimethoxy-6-methyltetrahydropyran | Zendy

Ruchi Srivastava | Zendy; R. K. Brown | Zendy

Open Access

Preparation of cis- and trans-2,5-dimethoxytetrahydropyran and cis- and trans-2,5-dimethoxy-6-methyltetrahydropyran

Author(s) -

Ruchi Srivastava,

R. K. Brown

Publication year - 1970

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v70-390

Subject(s) - chemistry , hydroboration , pyran , tetrahydropyran , medicinal chemistry , catalysis , gas chromatography , organic chemistry , stereochemistry , chromatography , ring (chemistry)

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.

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