Diethoxymethane → 17,21-Diacetoxy-6-methylene-4-pregnene-3,20-dione

HRID 2059163Notes

Reaction equation

[C:1]([O:4][C@:5]1([C@:29]2([CH3:30])[C@H:15]([C@H:16]3[C@H:26]([CH2:27][CH2:28]2)[C@:24]2([CH3:25])[C:19](=[CH:20][C:21](=[O:31])[CH2:22][CH2:23]2)[CH2:18][CH2:17]3)[CH2:14][CH2:13]1)[C:6](=[O:12])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].[CH2:32](OCOCC)C>>[C:1]([O:4][C@:5]1([C@:29]2([CH3:30])[C@H:15]([C@H:16]3[C@H:26]([CH2:27][CH2:28]2)[C@:24]2([CH3:25])[C:19](=[CH:20][C:21](=[O:31])[CH2:22][CH2:23]2)[C:18](=[CH2:32])[CH2:17]3)[CH2:14][CH2:13]1)[C:6](=[O:12])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 10024Diethoxymethane

HCID 10216517,21-Bis(acetyloxy)pregn-4-ene-3,20-dione

Product 1

HCID 1295177117,21-Diacetoxy-6-methylene-4-pregnene-3,20-dione

Procedure

1.0 g of 17,21-diacetoxy-4-pregnene-3,20-dione is reacted analogously to Example 9 with formaldehyde diethylacetal, and worked up, thus obtaining 790 mg of 17,21-diacetoxy-6-methylene-4-pregnene-3,20-dione, mp 227°-228° C.

Sources & evidence

ORD record: ord-3bd8215f43874d39a10337c8dd0cc9d3
Source dataset: uspto-grants-1982_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04322349

Reaction notes

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