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  • A new efficient synthetic method for 2- and 4-hydroxy-17 alpha-ethynylestradiol.

A new efficient synthetic method for 2- and 4-hydroxy-17 alpha-ethynylestradiol.

Steroids (1990-11-01)
R G Xie, Q Y Chen, J Xie, H M Zhao
ABSTRACT

The reaction of ethyl magnesium bromide and 17 alpha-ethynylestradiol with formaldehyde in the presence of triethyl phosphate or hexamethylphosphoramide gave the 2- and 4-formyl-17 alpha-ethynylestradiol in high yield. Treatment of the formyl derivatives with an alkaline solution of hydrogen peroxide in tetrahydrofuran afforded the corresponding catechols in almost quantitative yield. This new synthetic method was far superior to other methods, especially concerning simplicity, selectivity, and high yields.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Ethylmagnesium bromide solution, 1.0 M in tert-butyl methyl ether
Sigma-Aldrich
Ethylmagnesium bromide solution, 3.0 M in diethyl ether
Sigma-Aldrich
Ethylmagnesium bromide solution, 1.0 M in THF
Sigma-Aldrich
Ethylmagnesium bromide solution, 3.4 M in 2-methyltetrahydrofuran
Sigma-Aldrich
Ethylmagnesium bromide solution, 40% in 2-methyltetrahydrofuran