Nitric Acid → HCID 70627855, compound

HRID 1679763Notes

Reaction equation

HRID 1679763 reaction equation
[N+:1]([O-:4])([OH:3])=[O:2].O[C@@H:6]1[C@H:12]2[C@H:13]3[C@H:22]([CH2:23][CH2:24][C@:9]2([CH2:10][CH3:11])[C:8](=[O:26])[CH2:7]1)[C@@H:21]1[C:16](=[CH:17][C:18](=[O:25])[CH2:19][CH2:20]1)[CH2:15][CH2:14]3.C(OC(=O)C)(=O)C>>[CH3:11][CH2:10][C@:9]12[CH2:24][CH2:23][C@H:22]3[C@@H:13]([CH2:14][CH2:15][C:16]4[C@@H:21]3[CH2:20][CH2:19][C:18](=[O:25])[CH:17]=4)[C@@H:12]1[C@@H:6]([O:2][N+:1]([O-:4])=[O:3])[CH2:7][C:8]2=[O:26]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 15513180(15α)-13-Ethyl-15-hydroxygon-4-ene-3,17-dione

Product 1

HCID 70627855HCID 70627855, compound

Procedure

At -20° C., 6 ml. of concentrated nitric acid is added dropwise to 8.0 g. of 15α-hydroxy-18-methyl-4-estrene-3,17-dione in 60 ml. of acetic anhydride. After 1 hour, the reaction solution is introduced into ice/water. The thus-precipitated product is vacuum-filtered, washed several times with water, taken up in methylene chloride, and dried over sodium sulfate. After chromatographing the crude product on silica gel with acetone-hexane, 6.4 g. of 18-methyl-15α-nitrooxy-4-estrene-3,17-dione is produced.

Workup

  1. customAt -20° C.
  2. filtrationThe thus-precipitated product is vacuum-filtered
  3. washwashed several times with water
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-31fc8b2ea067471fafac1dd616a97f18
Source dataset
uspto-grants-1978_03
Patent number
US04081537

Reaction notes

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