Acetic Anhydride → HCID 68144275, compound

HRID 1731018Notes

Reaction equation

HRID 1731018 reaction equation
[OH:1][C@H:2]1[C@@H:8]2[CH2:9][C@@H:7]2[C@H:6]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:3]12[CH2:4][CH3:5])[C@@H:18]1[C:13](=[CH:14][C:15](=[O:22])[CH2:16][CH2:17]1)[CH2:12][CH2:11]3.[C:23](OC(=O)C)(=[O:25])[CH3:24]>N1C=CC=CC=1>[C:23]([O:1][C@H:2]1[C@@H:8]2[CH2:9][C@@H:7]2[C@H:6]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:3]12[CH2:4][CH3:5])[C@@H:18]1[C:13](=[CH:14][C:15](=[O:22])[CH2:16][CH2:17]1)[CH2:12][CH2:11]3)(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 68915450HCID 68915450, compound

Product 1

HCID 68144275HCID 68144275, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5.0 g. of natural 17β-hydroxy-18-methyl-15α,16α-methylene-4-estren-3-one is allowed to stand at room temperature in 20 ml. of pyridine and 10 ml. of acetic anhydride for 18 hours. The mixture is then stirred into ice water, the thus-obtained precipitate is filtered off and dissolved in methylene chloride. The methylene chloride phase is washed successively with dilute hydrochloric acid, water, sodium bicarbonate solution, and water. After drying and evaporation, 5.5 g. of natural 17β-acetoxy-18-methyl-15α,16α-methylene-4-estren-3-one is obtained.

Workup

  1. customto stand at room temperature in 20 ml
  2. filtrationthe thus-obtained precipitate is filtered off
  3. dissolutiondissolved in methylene chloride
  4. washThe methylene chloride phase is washed successively with dilute hydrochloric acid, water, sodium bicarbonate solution, and water
  5. customAfter drying
  6. customevaporation, 5.5 g

Sources & evidence

ORD record
ord-eea5c75861854e419add4a8b93a7b884
Source dataset
uspto-grants-1976_11
Patent number
US03994937

Reaction notes

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