Chloranil → HCID 15871130, compound

HRID 1861615Notes

Reaction equation

HRID 1861615 reaction equation
[OH:1][C@H:2]1[CH2:7][C@H:6]2[CH2:8][C@@:5]32[C@H:9]2[C@H:19]([CH2:20][CH2:21][C@:3]13[CH3:4])[C@:17]1([CH3:18])[C:12](=[CH:13][C:14](=[O:22])[CH2:15][CH2:16]1)[CH2:11][CH2:10]2.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C(O)(C)(C)C>[OH:1][C@H:2]1[CH2:7][C@H:6]2[CH2:8][C@@:5]32[C@H:9]2[C@H:19]([CH2:20][CH2:21][C@:3]13[CH3:4])[C@:17]1([CH3:18])[C:12](=[CH:13][C:14](=[O:22])[CH2:15][CH2:16]1)[CH:11]=[CH:10]2

Participants

4

Reactant 2

HCID 8371ChloranilHCID 15871129HCID 15871129, compound

Product 1

HCID 15871130HCID 15871130, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

1 g of 17β-hydroxy-14β,15β-methylen-androst-4-en-3-one (production, Example 2) is refluxed with 1.2 g of chloranil in 50 ml of tert-butanol for 30 minutes. It is allowed to cool and evaporated to the dry state. The residue is chromatographed on silica gel (mobile solvent: dichloromethane/ethyl acetate 10:1). For further purification, it is recrystallized from ethyl acetate.

Workup

  1. temperatureto cool
  2. customevaporated to the dry state
  3. customThe residue is chromatographed on silica gel (mobile solvent: dichloromethane/ethyl acetate 10:1)
  4. customFor further purification, it
  5. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6040d38970e64d6187ba229c178c4a5a
Source dataset
uspto-grants-2003_03
Patent number
US06534490B1

Reaction notes

Loading…