Water → HCID 67361620, compound

HRID 2413541Notes

Reaction equation

HRID 2413541 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][C@@H:11]1[C@H:17]2[C@H:18]3[C@H:27]([CH2:28][CH2:29][C@:14]2([CH2:15][CH3:16])[C:13](=[O:31])[CH2:12]1)[C@@H:26]1[C:21](=[CH:22][C:23](=[O:30])[CH2:24][CH2:25]1)[CH2:20][CH2:19]3.O>N1C=CC=CC=1.C(Cl)Cl>[C:1]([O:10][C@@H:11]1[C@H:17]2[C@H:18]3[C@H:27]([CH2:28][CH2:29][C@:14]2([CH2:15][CH3:16])[C:13](=[O:31])[CH2:12]1)[C@@H:26]1[C:21](=[CH:22][C:23](=[O:30])[CH2:24][CH2:25]1)[CH2:20][CH2:19]3)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

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 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

At 0° C., 5 ml of benzoyl chloride is added dropwise to 5 g of 15α-hydroxy-18-methyl-4-estrene-3,17-dione in 20 ml of pyridine. After 45 minutes, 2 ml of water is added, the mixture is stirred for another 30 minutes, and then the reaction mixture is poured into ice/water. The thus-precipitated product is suctioned off, dissolved in methylene chloride, washed with water, and dried over sodium sulfate. After chromatography of the crude product on silica gel with an acetone-hexane gradient, 5.6 g of 15α-benzoyloxy-18-methyl-4-estrene-3,17-dione is obtained as a foam.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-94509f0a72384023a72b1a4b21d0aefe
Source dataset
uspto-grants-1988_01
Patent number
US04719054

Reaction notes

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