2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 70543959, compound

HRID 1156049Notes

Reaction equation

HRID 1156049 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([CH2:11][CH3:12])[CH2:9][C@H:8]2[C@H:13]3[C:22](=[CH:23][CH2:24][C@:6]12[CH3:7])[C:21]1[CH2:20][CH2:19][C:18](=[O:25])[CH2:17][C:16]=1[CH2:15][CH2:14]3)(=[O:3])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1.C(Cl)Cl>[C:1]([O:4][C@H:5]1[C@H:10]([CH2:11][CH3:12])[CH2:9][C@H:8]2[C@H:13]3[C:22]([CH:23]=[CH:24][C@:6]12[CH3:7])=[C:21]1[C:16](=[CH:17][C:18](=[O:25])[CH2:19][CH2:20]1)[CH2:15][CH2:14]3)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 22820398HCID 22820398, compound

Product 1

HCID 70543959HCID 70543959, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

3.2 g of 17β-acetoxy-16α-ethyl-5(10),9(11)-estradien-3-one is dissolved in 120 ml of toluene and 40 ml of methylene chloride and combined at room temperature dropwise with a solution of 5.5 g of dichlorodicyano-p-benzoquinone in 80 ml of toluene and 20 ml of methylene chloride. The mixture is stirred for 16 hours at room temperature, filtered over neutral aluminum oxide, and concentrated. After crystallization from diethyl ether, 2.8 g of 17β-acetoxy-16α-ethyl-4,9,11-estratrien-3-one is obtained, m.p. 95°-98° C.

Workup

  1. filtrationfiltered over neutral aluminum oxide
  2. concentrationconcentrated
  3. customAfter crystallization from diethyl ether

Sources & evidence

ORD record
ord-0a798ff6753a4d44856a5f2ac89f70fe
Source dataset
uspto-grants-1982_06
Patent number
US04333928

Reaction notes

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