Sodium Hydroxide → HCID 88626365, compound

HRID 1193467Notes

Reaction equation

HRID 1193467 reaction equation
[CH2:1]1[C@@H:3]2[C:4](=[O:23])[CH:5]=[C:6]3[C@:19]([CH3:20])([CH:2]12)[C@@H:18]1[C@H:9]([C@H:10]2[C@@:14]([CH2:16][CH2:17]1)([CH3:15])[C:13](=[O:21])[CH2:12][CH2:11]2)[CH2:8][C:7]3=[CH2:22].[OH-:24].[Na+]>CO>[CH2:1]1[C@@H:3]2[C:4](=[O:23])[CH:5]3[O:24][C:6]43[C@:19]([CH3:20])([CH:2]12)[C@@H:18]1[C@H:9]([C@H:10]2[C@@:14]([CH2:16][CH2:17]1)([CH3:15])[C:13](=[O:21])[CH2:12][CH2:11]2)[CH2:8][C:7]4=[CH2:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66852514HCID 66852514, compound

Product 1

HCID 88626365HCID 88626365, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

1,2β-methylen-6-methylenandrost-4-ene-3,17-dione (3.104 g, 10 mmol) is dissolved in 120 ml of methanol and cooled to 0° C. Thereupon ice cold 36% H2O2 (10 ml) and 2% NaOH (5 ml) is added gradually, the reaction mixture kept for about 20 hours at 5° C. and then poured into 900 ml of ice water. The raw product is filtered off, washed with water, dried and then chromatographed on silica gel using CHCl3 as eluant. Thus pure title compound is obtained in 60% yield (1.959 g).

Workup

  1. filtrationThe raw product is filtered off
  2. washwashed with water
  3. customdried
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-eb522fa9fbea44b7b0a53fd0c926602c
Source dataset
uspto-grants-1989_03
Patent number
US04810423

Reaction notes

Loading…