Process of preparing ethylidene compounds

Abstract

Abstract PROCESS OF PREPARING ETHYLIDENE COMPOUNDS WITH DIFFERENT FUNDAMENTAL OR PARENT SUBSTANCES HAVING THE STRUCTURAL FORMULA: CH3-CH=C(-CH3)2 WHEREIN R1 AND R2 EACH REPRESENT A SATURATED OR UNSATURATED ALIPHATIC GROUP WHICH CAN BE SUBSTITUTED BY FUNCTIONAL GROUPS AND WHEREIN R1 AND R2 TAKEN TOGETHER CAN FORM AN ALICYCLIC GROUP SUCH AS CYCLOPENTYL, CYCLOHEXYL AND THE LIKE, OR R1 AND R2 CAN BE JOINED TOGETHER TO FORM A CONDENSED HYROAROMATIC GROUP SUCH AS A PERHYDROINDANE, CYCLOPENTANO-PERHYDRONAPHTALINE OR CYCLOPENTANO-PERHYDROPHENANTHRENE GROUP, WHEREBY THE C-C BOUNDS OF THE PARENT SUBSTANCE ARE PREFERABLY UNSATURATED AND IN STEROID COMPOUNDS THE RING OF THE BASIC STRUCTURE CAN BE JOINED IN EITHER THE CIS- OR TRANSFORM WHICH COMPRISES REACTING AN EASILY HYDOLYZABLE DERIVATIVE OF VINYL AND ETHINYL CARBINOL, AS FOR INSTANCE AN ETHER, HAVING THE FORMULA: R4-O-C(-R1)(-R2)-R3 WHEREIN R1 AND R2 ARE AS ABOVE DEFINED AND R3 IS VINYL OR ETHINYL AND R4 IS A TRIALKYLSILYL OR TETRAHYDROPYANYL GROUP WITH AN ALKALI METAL IN THE PRESENCE OF A PROTON DONOR AND LIQUID AMMONIA. THESE COMPOUNDS ARE PARTICULARLY ADAPTED FOR USE AS INTERMEDIATES FOR USE IN PREPARING HIGHLY ACTIVE STEROID COMPOUNDS, AS FOR EXAMPLE, 19-NOR PREGNANE DERIVATIVES.

Inventors

• 👤 Gerhard Teichmuller
• 👤 Werner Hartmann

Bibliographic Details