Acta Cryst. (2012). E68, o3331
[ doi:10.1107/S1600536812045278 ]

Westphalen's diol diacetate: 19(105)-abeo-5-cholest-9-ene-3,6-diyl diacetate

J. Ramírez Hernández, J. Sandoval-Ramírez, S. Meza-Reyes, J. L. Vega Báez and S. Bernès

Abstract: The structure of the title steroid [alternative name: 3,6-diacetoxy-5-methyl-19-norcholest-9(10)-ene], C₃₁H₅₀O₄, confirms the generally accepted mechanism for the rearrangement of a cholestan-5-ol derivative reported a century ago by Westphalen. The methyl group at position 10 of the starting material migrates to position 5 in the steroidal nucleus, while a ⁹ bond is formed, as indicated by the C=C bond length of 1.347 (4) Å. The methyl transposition leaves the 5R configuration unchanged, with the methyl oriented towards the face. During the rearrangement, the steroidal B ring experiences a conformational distortion from chair to envelope with the C atom at position 6 as the flap. In the title structure, the isopropyl group of the side chain is disordered over two positions, with occupancies of 0.733 (10) and 0.267 (10). The carbonyl O atom in the acetyl group at C3 is also disordered with an occupancy ratio of 0.62 (4):0.38 (4).

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