Cholesterol → 1,4,6-Cholestatrien-3-one

HRID 444409

Reaction equation

HRID 444409 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:27]2([CH3:28])[C@H:12]([C@H:13]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:16]([CH2:17][C@H:18]([CH2:20][CH2:21]2)[OH:19])=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:27]2([CH3:28])[C@H:12]([C@H:13]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:16](=[CH:17][C:18](=[O:19])[CH:20]=[CH:21]2)[CH:15]=[CH:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

Participants

4

Reactant 2

HCID 5997CholesterolHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone

Product 1

HCID 1073901,4,6-Cholestatrien-3-oneYield 56%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1,4,6-cholestatrien-3 one was prepared in 56% yield from cholesterol, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and dioxane by the procedure of A. B. Turner J. Chem. Soc. C, 2568 (1968).

Sources & evidence

ORD record
ord-783a3b8375f74c19a65838b24427a38f
Source dataset
uspto-grants-1981_04
Patent number
US04264512

Linked notes

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