Sodium Hydroxide → HCID 54122970, compound

HRID 274310Notes

Reaction equation

HRID 274310 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-792656adb1d34ef2853d1ee6418ee774
Source dataset
uspto-grants-1995_02
Patent number
US05389624

Reaction notes

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