2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 68595634, compound

HRID 1970930Notes

Reaction equation

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

Participants

Reactant 2

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

HCID 68597279HCID 68597279, compound

Product 1

HCID 68595634HCID 68595634, compoundYield 50.2%

Procedure

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

Workup

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

Sources & evidence

ORD record: ord-986745dd4d244ac6aa438e03d97f8520
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431554B2

Reaction notes

Loading…