17,17-Bis(ethylendioxy)-6-methyleneandrostane → 17,17-Bis(ethylendioxy)-6alpha-vinylandrostane

HRID 42097Notes

Reaction equation

HRID 42097 reaction equation
[CH2:1]1COC23OCCOC2([C@]2(CC[C@H]4[C@@H](C[C@H](C=O)C5[C@]4(C)CCCC5)[C@@H]2C3)C)O1.[CH2:30]1[CH2:43][O:42][C:37]23[O:38][CH2:39][CH2:40][O:41][C:32]2([C@:33]2([CH2:56][CH2:55][C@H:54]4[C@@H:44]([CH2:45][C:46](=[CH2:57])[CH:47]5[C@:52]4([CH3:53])[CH2:51][CH2:50][CH2:49][CH2:48]5)[C@@H:35]2[CH2:36]3)[CH3:34])[O:31]1>>[CH2:40]1[CH2:39][O:38][C:37]23[O:42][CH2:43][CH2:30][O:31][C:32]2([C@:33]2([CH2:56][CH2:55][C@H:54]4[C@@H:44]([CH2:45][C@H:46]([CH:57]=[CH2:1])[CH:47]5[C@:52]4([CH3:53])[CH2:51][CH2:50][CH2:49][CH2:48]5)[C@@H:35]2[CH2:36]3)[CH3:34])[O:41]1

Participants

3

Reactant 2

HCID 6753593917,17-Bis(ethylendioxy)-6-methyleneandrostaneHCID 8663556717,17-Bis(ethylendioxy)-6alpha-formylandrostane

Product 1

HCID 8663557417,17-Bis(ethylendioxy)-6alpha-vinylandrostaneYield 70%

Procedure

17,17-Bis(ethylendioxy)-6α-vinylandrostane was prepared in 70% yield from 3,3:17,17-bis(ethylendioxy)-6α-formylandrostane (Prepn. 14) by the procedure described above for the preparation of 3,3:17,17-bis(ethylendioxy)-6-methyleneandrostane (Prepn. 13). The crude was purified by flash chromatography (SiO2, n-hexane/EtOAc 88/12). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 5.47 (1H, m), 4.91 (2H, m), 3.94-3.73 (8H, m), 2.00-0.67 (21H, m), 0.88 (3H, s), 0.83 (3H, s).

Workup

  1. customThe crude was purified by flash chromatography (SiO2, n-hexane/EtOAc 88/12)

Sources & evidence

ORD record
ord-b0293b5fc30f43b7b50295030b835a83
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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