Pyridine → 3alpha-Trichloroacetoxy-5alpha-pregnane-11,20-dione

HRID 1606469Notes

Reaction equation

HRID 1606469 reaction equation
[Cl:1][C:2]([Cl:7])([Cl:6])[C:3](Cl)=[O:4].[OH:8][C@@H:9]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@@H:11]([CH2:12][CH2:13][C@@H:14]3[C@@H:25]2[C:24](=[O:30])[CH2:23][C@@:22]2([CH3:31])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C:19](=[O:21])[CH3:20])[CH2:10]1.N1C=CC=CC=1>O1CCCC1>[Cl:1][C:2]([Cl:7])([Cl:6])[C:3]([O:8][C@@H:9]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@@H:11]([CH2:12][CH2:13][C@@H:14]3[C@@H:25]2[C:24](=[O:30])[CH2:23][C@@:22]2([CH3:31])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C:19](=[O:21])[CH3:20])[CH2:10]1)=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6420Trichloroacetyl chlorideHCID 104845Alphaxalone

Product 1

HCID 867333203alpha-Trichloroacetoxy-5alpha-pregnane-11,20-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of trichloroacetyl chloride (0.5 ml.) in dry tetrahydrofuran (8 ml.) was added dropwise to a cooled (-80°) and stirred solution of 3α-hydroxy-5α-pregnane-11,20-dione (0.75 g.) and pyridine (0.35 ml.) in dry tetrahydrofuran (15 ml.). After 30 min. the mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with 2N-hydrochloric acid, aqueous sodium hydrogen carbonate, then water. The solution was dried and concentrated to leave a residue which was crystallised from benzene then benzene-petrol to afford the title compound (0.21 g.), m.p. 126°-127°, [α]D + 86°.

Workup

  1. temperaturea cooled (-80°)
  2. concentrationAfter 30 min. the mixture was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with 2N-hydrochloric acid, aqueous sodium hydrogen carbonate
  5. customThe solution was dried
  6. concentrationconcentrated
  7. customto leave a residue which
  8. customwas crystallised from benzene

Sources & evidence

ORD record
ord-8d348707131143868dccc24c7b45d4cf
Source dataset
uspto-grants-1976_04
Patent number
US03953429

Reaction notes

Loading…