2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Cholesta-1,4,6-triene-3,24-dione

HRID 2397949Notes

Reaction equation

HRID 2397949 reaction equation
[O:1]=[C:2]([CH2:6][CH2:7][C@H:8]([C@@H:10]1[C@:28]2([CH3:29])[C@H:13]([C@H:14]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:17]([CH2:18][C@H:19]([CH2:21][CH2:22]2)[OH:20])=[CH:16][CH2:15]3)[CH2:12][CH2:11]1)[CH3:9])[CH:3]([CH3:5])[CH3:4].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH3:5][CH:3]([C:2](=[O:1])[CH2:6][CH2:7][C@H:8]([C@@H:10]1[C@:28]2([CH3:29])[C@H:13]([C@H:14]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:17](=[CH:18][C:19](=[O:20])[CH:21]=[CH:22]2)[CH:16]=[CH:15]3)[CH2:12][CH2:11]1)[CH3:9])[CH3:4]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 1103680824-Ketocholesterol

Product 1

HCID 54483961Cholesta-1,4,6-triene-3,24-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Fucosterol is oxidized with ozone at low temperatures, and the resulting ozonide is reduced with an acetic acid/zinc system to form 24-ketocholesterol of the following formula ##STR15## in a yield of about 60 to 75%. The resulting 24-ketocholesterol is oxidized, for example, with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) under reflux of, for example, dioxane to form cholesta-1,4,6-triene-3,24-dione of the following formula ##STR16## and then this oxidation product is epoxidized at room temperature under alkaline conditions (pH about 7.5-9) using hydrogen peroxide, for example.

Sources & evidence

ORD record
ord-85c3423a8a9e42fa899d6ac56854283f
Source dataset
uspto-grants-1977_05
Patent number
US04022891

Reaction notes

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