Water → HCID 86733326, compound

HRID 1606480Notes

Reaction equation

HRID 1606480 reaction equation
C([O:4][C@@H:5]1[CH:24]=[CH:23][C@@:22]2([CH3:25])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[C:20](=[O:26])[CH2:19][C@@:18]2([CH3:27])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=O)C.[OH-].[K+].O>CO>[OH:4][C@@H:5]1[CH:24]=[CH:23][C@@:22]2([CH3:25])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[C:20](=[O:26])[CH2:19][C@@:18]2([CH3:27])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 86733327HCID 86733327, compound

Product 1

HCID 86733326HCID 86733326, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of crude 3α-acetoxy-5α-pregn-1-ene-11,20-dione (3.6 g.) in dry methanol (96 ml.) was treated with a solution of potassium hydroxide (650 mg.) in methanol (72 ml.), and the mixture stirred under nitrogen at room temperature for 2 hr. The reaction mixture was poured into water, and the product extracted with methylene chloride. The extract was washed with water, dried (MgSO4), and evaporated in vacuo. The residue (3.1 g.) was subjected to preparative t.l.c. The more polar product afforded the title compound (1.66 g.), with an RF identical on t.l.c. to that of the product of (a).

Workup

  1. extractionthe product extracted with methylene chloride
  2. washThe extract was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-01d14a5eae87400891ce25a7bb88f87f
Source dataset
uspto-grants-1976_04
Patent number
US03953429

Reaction notes

Loading…