Benzoyl chloride → 15alpha-Benzoyloxyestra-4,9-diene-3,17-dione

HRID 329382Notes

Reaction equation

HRID 329382 reaction equation
[OH:1][C@@H:2]1[C@H:7]2[C@H:8]3[C:17]([CH2:18][CH2:19][C@:5]2([CH3:6])[C:4](=[O:21])[CH2:3]1)=[C:16]1[C:11](=[CH:12][C:13](=[O:20])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1>[C:22]([O:1][C@@H:2]1[C@H:7]2[C@H:8]3[C:17]([CH2:18][CH2:19][C@:5]2([CH3:6])[C:4](=[O:21])[CH2:3]1)=[C:16]1[C:11](=[CH:12][C:13](=[O:20])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 1342360815alpha-Hydroxy-4,9-estradiene-3,17-dione

Product 1

HCID 5661194015alpha-Benzoyloxyestra-4,9-diene-3,17-dione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 20 g of 15α-hydroxyestra-4,9-diene-3,17-dione in 120 ml of pyridine is combined dropwise with 13.6 ml of benzoyl chloride and the mixture is stirred for one hour at room temperature. Subsequently the mixture is poured into ice water, extracted with dichloromethane, washed with sodium bicarbonate solution and water and concentrated under vacuum. The cooled crude product is chromatographed on silica gel, yielding 26.2 g of 15α-benzoyloxyestra-4,9-diene-3,17-dione.

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with sodium bicarbonate solution and water
  3. concentrationconcentrated under vacuum
  4. temperatureThe cooled crude product
  5. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-6f4ee7e382d24588bccd527460a495cb
Source dataset
uspto-grants-1990_01
Patent number
US04891365

Reaction notes

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