Elin King

Publication Date

1972

Document Type

Dissertation/Thesis

First Advisor

Piatak, David M.

Degree Name

M.S. (Master of Science)

Legacy Department

Department of Chemistry

LCSH

Esters; Ethers; Cholanic acid

Abstract

A study of the ester to ether reduction by sodium boro-hydride-boron trifluoride etherate with four different cholinic acid esters was made to test this reduction reaction in the presence of other functional groups. To prepare the esters from 3d-hydroxy-5B-cholan-24-oic acid the 3d-hydroxyl moiety was first protected. This was accomplished by forming the nitrate ester with fuming nitric acid-acetic anhydride. The resulting 5B-cholan-24-oic acid 3d-nitrate was then converted into its acid chloride with oxalyl chloride or thionyl chloride, and from this acid chloride nitrate, the isopropyl, isobutyl, t-butyl, and t-amyl esters were obtained by dissolving it in a mixture of the corresponding alkyl alcohols and pyridine. The resulting esters XXa-d were then reduced catalytically to remove the nitrate moiety. The 3d-hydroxy esters XXIa-d thus obtained were then treated with the sodium borohydride-boron trifluoride etherate reagent. If was found that very little ether was formed and that the major product from each of the esters was 3d, 24-dihydroxy-5B-cholane. A study of the mass spectra of a few of the esters was also made.

Comments

Includes bibliographical references (pages [44]-49)

Extent

49 pages

Language

eng

Publisher

Northern Illinois University

Rights Statement

In Copyright

Rights Statement 2

NIU theses are protected by copyright. They may be viewed from Huskie Commons for any purpose, but reproduction or distribution in any format is prohibited without the written permission of the authors.

Media Type

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