Water → HCID 70564353, compound

HRID 848786Notes

Reaction equation

HRID 848786 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C@H:12]([CH2:13][C:14](=[O:24])[C:15](=[CH:22][OH:23])[CH2:16]1)[CH2:11][CH2:10]3.N1[CH:30]=[CH:29]C=CC=1.[OH2:31]>C(OC(=O)C)(=O)C>[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C@H:12]([CH2:13][C:14](=[O:24])[C:15](=[CH:22][O:23][C:29](=[O:31])[CH3:30])[CH2:16]1)[CH2:11][CH2:10]3

Participants

5

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 70565755HCID 70565755, compound

Product 1

HCID 70564353HCID 70564353, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 17β-methoxy-2-hydroxymethylen-5α-androstan-3-one (U.S. Pat. No. 3,980,638, Example 3, 0.5 gm.) in acetic anhydride (3.0 ml.) and pyridine (3 ml.) is allowed to stand at 20°-25° for 24 hours. The reaction mixture is then poured into water and the product separates. The product is collected and dissolved in benzene and purified by column chromatography on Florisil. The appropriate fractions (TLC) are pooled and concentrated to give a residue. The residue is crystallized from methanol to give 17β-methoxy-2-acetoxymethylen-5α-androstan-3-one.

Workup

  1. customThe product is collected
  2. dissolutiondissolved in benzene
  3. custompurified by column chromatography on Florisil
  4. concentrationconcentrated
  5. customto give a residue
  6. customThe residue is crystallized from methanol

Sources & evidence

ORD record
ord-97fd8db3f770494399200dd04682e0b2
Source dataset
uspto-grants-1981_10
Patent number
US04297350

Reaction notes

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