2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 68596099, compound

HRID 1970931Notes

Reaction equation

[OH:1][C@@H:2]1[C:30]2[C@:25]([CH3:32])([CH2:26][CH2:27][C:28](=[O:31])[CH:29]=2)[C@@H:24]2[C@H:4]([C@H:5]3[C@:21]([CH3:33])([CH2:22][CH2:23]2)[C@@H:8]([C@H:9]([CH3:20])[C@H:10]([OH:19])[C@@H:11]([OH:18])[C@H:12]([CH:15]([CH3:17])[CH3:16])[CH2:13][CH3:14])[CH2:7][CH2:6]3)[CH2:3]1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>>[OH:1][C@@H:2]1[C:30]2[C@:25]([CH3:32])([CH:26]=[CH:27][C:28](=[O:31])[CH:29]=2)[C@@H:24]2[C@H:4]([C@H:5]3[C@:21]([CH3:33])([CH2:22][CH2:23]2)[C@@H:8]([C@H:9]([CH3:20])[C@H:10]([OH:19])[C@@H:11]([OH:18])[C@H:12]([CH:15]([CH3:17])[CH3:16])[CH2:13][CH3:14])[CH2:7][CH2:6]3)[CH2:3]1

Participants

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone

HCID 68594549HCID 68594549, compound

Product 1

HCID 68596099HCID 68596099, compoundYield 70.3%

Procedure

50 mg of (22S,23S)-6α,22,23-trihydroxystigmast-4-en-3-one are treated with DDQ following the procedure described in Example 6. After purification by silica column chromatography (eluting solvent: hexane/ethyl acetate 8:2) of the crude product obtained, 35 mg of (22S,23S)-6α,22,23-trihydroxystigmasta-1,4-dien-3-one are isolated.

Workup

customAfter purification
washby silica column chromatography (eluting solvent: hexane/ethyl acetate 8:2) of the crude product
customobtained

Sources & evidence

ORD record: ord-c5c440b968724902829cfcc61793e021
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431554B2

Reaction notes

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