Benzene → HCID 13044098, compound

HRID 1701488Notes

Reaction equation

HRID 1701488 reaction equation
[OH:1][CH2:2][C@@H:3]([CH3:24])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][CH2:15]2)[CH:10]=[CH:9]3)[CH2:6][CH2:5]1.C1C=CC=CC=1>C(Cl)Cl>[OH:1][CH2:2][C@@H:3]([CH3:24])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH:14]=[CH:15]2)[CH:10]=[CH:9]3)[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 241BenzeneHCID 13044132HCID 13044132, compound

Product 1

HCID 13044098HCID 13044098, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.7 g. of (20S)-21-hydroxy-20-methylpregna-4,6-dien-3-one in 80 ml. of dry benzene was treated with 1.45 g. of dichlorodicyano and then heated under reflux for 10 hours. The resulting suspension was filtered under suction, the filtrate was washed with 5% sodium hydroxide, then with water and dried over sodium sulfate. The residue obtained by evaporation was taken up in methylene chloride and filtered through a column of 10 g. of aluminum oxide. From the filtrate, 1 g. of crude crystals were obtained, were recrystallized from ether to give (20S)-21-hydroxy-20-methylpregna-1,4,6-trien-3-one, m.p. 156°-157°. This was shown to be identical to the compound obtained in Example 8 according to its thin layer chromatogram mixture, melting point and infrared spectrum.

Workup

  1. temperatureof dichlorodicyano and then heated
  2. temperatureunder reflux for 10 hours
  3. filtrationThe resulting suspension was filtered under suction
  4. washthe filtrate was washed with 5% sodium hydroxide
  5. dry with materialwith water and dried over sodium sulfate
  6. customThe residue obtained by evaporation
  7. filtrationfiltered through a column of 10 g
  8. customof crude crystals were obtained
  9. customwere recrystallized from ether

Sources & evidence

ORD record
ord-f2f76cdf45da4d3596c9d8807af4cb39
Source dataset
uspto-grants-1980_03
Patent number
US04193921

Reaction notes

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