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Borohydride Reduction of Estrone. Demonstration of Diastereoselectivity in the Undergraduate Organic Chemistry Laboratory

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Animesh Aditya , David E. Nichols and G. Marc Loudon

Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, IN 47907

J. Chem. Educ., 2008, 85 (11), p 1535

DOI: 10.1021/ed085p1535

Publication Date (Web): November 1, 2008

Section:

History, Education, and Documentation

Abstract

This experiment presents a guided-inquiry approach to the demonstration of diastereoselectivity in an undergraduate organic chemistry laboratory. Chiral hindered ketones such as estrone, undergo facile reduction with sodium borohydride in a highly diastereoselective manner. The diastereomeric estradiols produced in the reaction can be analyzed and differentiated by thin-layer chromatography and melting point.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Problem Solving / Decision Making

Keywords (Subject):

Aldehydes / Ketones

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History

Received: August 03, 2009

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Article

Borohydride Reduction of Estrone. Demonstration of Diastereoselectivity in the Undergraduate Organic Chemistry Laboratory

Abstract

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Keywords (Domain):

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Keywords (Subject):

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History

Recommend & Share

Related Content

The Synthesis of N-Benzyl-2-azanorbornene via Aqueous Hetero Diels–Alder Reaction. An Undergraduate Project in Organic Synthesis and Structural Analysis

A One-Pot, Asymmetric Robinson Annulation in the Organic Chemistry Majors Laboratory

Regioselectivity in Organic Synthesis: Preparation of the Bromohydrin of alpha-Methylstyrene

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