Phenylseleninyl benzeneseleninate → HCID 18632049, compound

HRID 621627Notes

Reaction equation

HRID 621627 reaction equation
[O:1]1[C:3]23[C@:16]([CH3:22])([C@H:17]([CH3:21])[CH2:18][C:19](=[O:20])[CH:2]12)[C@@H:15]1[C@H:6]([C@H:7]2[C@@:11]([CH2:13][CH2:14]1)([CH3:12])[C:10](=[O:23])[C@H:9]([F:24])[CH2:8]2)[C:5](=[CH2:25])[C@H:4]3[CH3:26].C1([Se](O[Se](C2C=CC=CC=2)=O)=O)C=CC=CC=1>ClC1C=CC=CC=1>[O:1]1[C:3]23[C@:16]([CH3:22])([C:17]([CH3:21])=[CH:18][C:19](=[O:20])[CH:2]12)[C@@H:15]1[C@H:6]([C@H:7]2[C@@:11]([CH2:13][CH2:14]1)([CH3:12])[C:10](=[O:23])[C@H:9]([F:24])[CH2:8]2)[C:5](=[CH2:25])[C@H:4]3[CH3:26]

Participants

4

Reactant 2

HCID 87253Phenylseleninyl benzeneseleninateHCID 18632050HCID 18632050, compound

Product 1

HCID 18632049HCID 18632049, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of 4,5-epoxy-16α-fluoro-1β,6β-dimethyl-7-methylenandrostane-3,17-dione (361 mg) and benzeneseleninic anhydride (360 mg) in chlorobenzene (30 ml) is heated for 4 hrs at 90°-100° C. Then the solvent is removed in vacuo and the residue chromatographed on silica gel to give 4,5-epoxy-16α-fluoro-1,6β-dimethyl-7-methylenandrost-1-ene-3,17-dione (287 mg).

Workup

  1. customThen the solvent is removed in vacuo
  2. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-82486baf9c944102a547a7b1bb15070a
Source dataset
uspto-grants-1989_04
Patent number
US04824830

Reaction notes

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