Process to prepare stabilized monolithium acetylide

Details Process to prepare stabilized monolithium acetylide Process to prepare stabilized monolithium acetylide

1984-01-05

1985-07-02

Roberts, Elbert L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

26039745, 2603975, 260665R, C07J 100

Patent

active

045267200

ABSTRACT:
The process of the present invention uses an amine to prepare monolithium acetylide which is sufficiently stable at up to 0.degree. and yet is sufficiently reactive to react with 16-substituted-17-keto steroids producing the useful 17.alpha.-ethynyl-17.beta.-hydroxy-16-substituted steroids.

REFERENCES:
patent: 4055562 (1977-10-01), Christiansen
Midland; "Journal of Organic Chemistry," vol. 40, No. 15, (1975), pp. 2250-2252.
J. Chem. Soc. 4765, (1956), "Researches on Acetylenic Compounds, Part LIV, The Preparation and Synthetical . . . ", by Jones, Skattebol and Whiting.
J. Mol. Structure 42, 251, (1977), by Moffat, "Linear Alkynes and the Effect on Bond Lengths of Chain . . . ".
J. Am. Chem. Soc. 98, 4778, (1976), by Streitwieser, "Ab Initio SCF-MO Calculations of Methyllithium and Related Systems . . . ".
Fieser & Fiester, Steroids, Reinhold Publishing Co., N.Y., 1959, pp. 557-591.
J. Am. Chem. Soc. 78, 2477, (1956), "Steroids . . . ", by H. J. Ringold et al.
J. Org. Chem. 34, 435, (1969), "Liquid Acetylene . . . ", by R. J. Tedeschi and G. L. Moore.
J. Org. Chem. 40, 2250, (1975), by Midland, "Preparation of Monolithium Acetylide in Tetrahydrofuran . . . ".
Chim. Ind. (Milan) 42, 251, (1960), M. Corbellini; L. Turner.
Chem. Abstr. 54, 19250, (1960).

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