Sodium Hydroxide → HCID 54122970, compound

HRID 2254631Notes

Reaction equation

HRID 2254631 reaction equation
O[C@@:2]1([CH3:23])[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C@:4]1([CH3:22])[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:21])[CH2:6][CH2:5]1.[OH-].[Na+]>C(O)=O>[CH2:23]=[C:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C@:4]1([CH3:22])[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:21])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67780748HCID 67780748, compound

Product 1

HCID 54122970HCID 54122970, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

9 g of 11β-hydroxy-11α-methylandrost-4-ene-3,17-dione is allowed to react with 100 ml of concentrated formic acid at 50° C. After 6 hours, the solution is stirred into ice/water that contains sodium hydroxide. The precipitated product is suctioned off, washed with water, dissolved in ethyl acetate, dried, and concentrated under vacuum. The crude product is chromatographed on silica gel with a methylene chloride-ethyl acetate gradient, thus obtaining 5 g of 11-methyleneandrost-4-ene-3,17-dione, mp 157°-160° C. (from acetone/hexane).

Workup

  1. washwashed with water
  2. dissolutiondissolved in ethyl acetate
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customThe crude product is chromatographed on silica gel with a methylene chloride-ethyl acetate gradient

Sources & evidence

ORD record
ord-354911a1de5d4286b5614fe16607fd25
Source dataset
uspto-grants-1993_08
Patent number
US05236912

Reaction notes

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