Reaction #70400

ord-c8c9487b74514d218f523c0f22b69599

Reaction equation

C[C@]12CCCCC1C[C@@H](C=O)[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)-7α-formylandrostane
C=C1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(C)CCC(=O)CC12
6-methyleneandrostane-3,17-dione
→
C[C@]12CCC(=O)CC1C[C@@H](C=O)[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
7α-Formylandrostane-3,17-dione
Yield 85.0%

Reactants

C[C@]12CCCCC1C[C@@H](C=O)[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC13OCCOC12OCCO3
17,17-bis(ethylendioxy)-7α-formylandrostane
C=C1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(C)CCC(=O)CC12
6-methyleneandrostane-3,17-dione

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

7α-Formylandrostane-3,17-dione was prepared in 85% yield from 3,3:17,17-bis(ethylendioxy)-7α-formylandrostane (2.36 g) by the procedure described above for the preparation of 6-methyleneandrostane-3,17-dione (II-ac, Prepn. 13). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 9.95 (1H, d), 2.57-0.80 (21H, m), 0.95 (3H, s), 0.80 (3H, s).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08536160B2uspto-grants-2013_09