2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 70544502, compound

HRID 1156052Notes

Reaction equation

HRID 1156052 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([CH2:11][CH2:12][CH3:13])[CH2:9][C@H:8]2[C@H:14]3[C:23](=[CH:24][CH2:25][C@:6]12[CH3:7])[C:22]1[CH2:21][CH2:20][C:19](=[O:26])[CH2:18][C:17]=1[CH2:16][CH2:15]3)(=[O:3])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(Cl)Cl>[C:1]([O:4][C@H:5]1[C@H:10]([CH2:11][CH2:12][CH3:13])[CH2:9][C@H:8]2[C@H:14]3[C:23]([CH:24]=[CH:25][C@:6]12[CH3:7])=[C:22]1[C:17](=[CH:18][C:19](=[O:26])[CH2:20][CH2:21]1)[CH2:16][CH2:15]3)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 22820401HCID 22820401, compound

Product 1

HCID 70544502HCID 70544502, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.5 g of 17β-acetoxy-16α-propyl-5(10),9(11)-estradien-3-one in 100 ml of methylene chloride is dehydrogenated with 1.8 g of dichlorodicyano-p-benzoquinone under the conditions of Example 1. After crystallization from diisopropyl ether, 1.4 g of 17β-acetoxy-16α-propyl-4,9,11-estratrien-3-one is obtained, m.p. 108°-109° C.

Workup

  1. customAfter crystallization from diisopropyl ether

Sources & evidence

ORD record
ord-86a6f5e699714ab788aa129b4ee7f097
Source dataset
uspto-grants-1982_06
Patent number
US04333928

Reaction notes

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