Water → HCID 67361620, compound

HRID 1380816Notes

Reaction equation

HRID 1380816 reaction equation
[OH:1][C@@H:2]1[C@H:8]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH2:6][CH3:7])[C:4](=[O:22])[CH2:3]1)[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>N1C=CC=CC=1>[C:23]([O:1][C@@H:2]1[C@H:8]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH2:6][CH3:7])[C:4](=[O:22])[CH2:3]1)[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 15513180(15α)-13-Ethyl-15-hydroxygon-4-ene-3,17-dione

Product 1

HCID 67361620HCID 67361620, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 102 g of 15α-hydroxy-18-methyl-4-estrene-3,17-dione in 500 ml of pyridine is combined under ice cooling with 50.9 ml of benzoyl chloride and stirred for one hour under cooling. Then 9 ml of water is added dropwise and the mixture is stirred for another hour. The reaction solution is then stirred into ice water, the thus-formed precipitate is suctioned off, washed with water, and dried, thus obtaining 146 g of crude 15α-benzoyloxy-18-methyl-4-estrene-3,17-dione.

Workup

  1. temperatureunder cooling
  2. stirringthe mixture is stirred for another hour
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-20c9c94c298a43cfb8c0764ffc9c82f7
Source dataset
uspto-grants-1986_04
Patent number
US04584288

Reaction notes

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