Chloranil → Methyl androst-4,6-diene-3one-17beta-carboxylate

HRID 477441

Reaction equation

HRID 477441 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[C:21]([O:23][CH3:24])=[O:22].C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C(O)(C)(C)C>[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH:8]=[CH:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[C:21]([O:23][CH3:24])=[O:22]

Participants

4

Reactant 2

HCID 8371ChloranilHCID 165014Methyl (17beta)-3-oxoandrost-4-ene-17-carboxylate

Product 1

HCID 10947441Methyl androst-4,6-diene-3one-17beta-carboxylate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Methyl androst-4-ene-3-one-17β-carboxylate (10 g, 30.3 mmol, prepared according to Rasmusson, et al., J. Med. Chem. 27 1960 (1984)) and chloranil (8.95 g, 36.4 mmol) in 700 ml t-butanol was heated at reflux for 3.5 hours then cooled and filtered. The filtrate was concentrated and the residue taken up in 700 ml chloroform and washed successively with 4×150 ml water, 3×150 ml saturated sodium bicarbonate, 3×150 ml 5% sodium hydroxide, 3×150 ml brine, dried over sodium sulfate, and concentrated to yield methyl androst-4,6-diene-3-one-17β-carboxylate as a dark foam (7.0 g, 70%).

Workup

  1. temperatureat reflux for 3.5 hours
  2. temperaturethen cooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. washwashed successively with 4×150 ml water, 3×150 ml saturated sodium bicarbonate, 3×150 ml 5% sodium hydroxide, 3×150 ml brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fe997bfe582646dcb83762d6198493ac
Source dataset
uspto-grants-1989_12
Patent number
US04888336

Linked notes

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