Dichloromethane → HCID 86738409, compound

HRID 1156051Notes

Reaction equation

HRID 1156051 reaction equation
[C:1]([C@:3]1([OH:23])[C@H:8]([CH3:9])[CH2:7][C@H:6]2[C@H:10]3[C:19](=[CH:20][CH2:21][C@:4]12[CH3:5])[C:18]1[CH2:17][CH2:16][C:15](=[O:22])[CH2:14][C:13]=1[CH2:12][CH2:11]3)#[CH:2].C(Cl)Cl.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1>[C:1]([C@:3]1([OH:23])[C@H:8]([CH3:9])[CH2:7][C@H:6]2[C@H:10]3[C:19]([CH:20]=[CH:21][C@:4]12[CH3:5])=[C:18]1[C:13](=[CH:14][C:15](=[O:22])[CH2:16][CH2:17]1)[CH2:12][CH2:11]3)#[CH:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 22820397HCID 22820397, compound

Product 1

HCID 86738409HCID 86738409, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1.9 g of 17α-ethynyl-17β-hydroxy-16α-methyl-5(10),9(11)-estradien-3-one is dissolved in 60 ml of benzene and 20 ml of methylene chloride and combined at room temperature dropwise with a solution of 3.5 g of dichlorodicyano-p-benzoquinone. The mixture is agitated for 5 hours at room temperature and worked up as described in Example A. Crystallization of ether yields 1.65 g of 17α-ethynyl-17β-hydroxy-16α-methyl-4,9,11-estratrien-3-one, m.p. 176°-179° C.

Workup

  1. customCrystallization of ether

Sources & evidence

ORD record
ord-f40a5b13e1584dcf966bbb67afae7d46
Source dataset
uspto-grants-1982_06
Patent number
US04333928

Reaction notes

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