Methanol → HCID 13371257, compound

HRID 280838Notes

Reaction equation

HRID 280838 reaction equation
C([O:4][CH2:5][C:6]1[C@@:23]2([CH3:24])[C:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@H:14]3[CH2:15][CH2:16][C:17]2=[O:25])=[CH:9][C:8](=[O:26])[CH:7]=1)(=O)C.CO.[OH-].[K+]>C(Cl)Cl>[OH:4][CH2:5][C:6]1[C@@:23]2([CH3:24])[C:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@H:14]3[CH2:15][CH2:16][C:17]2=[O:25])=[CH:9][C:8](=[O:26])[CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 54045133HCID 54045133, compound

Product 1

HCID 13371257HCID 13371257, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.2 g of 1-acetoxymethylandrosta-1,4-diene-3,17-dione is stirred under argon gas atmosphere in 20 ml of methylene chloride and 25 ml of methanol with 250 mg of potassium hydroxide at 0° to 5° C. for 5 hours. The mixture is then neutralized with acetic acid, concentration, and precipitated into water. The product is suctioned off, washed with water, and dried. Recrystallization from acetone/hexane yields 1.7 g of 1-hydroxymethylandrosta-1,4-diene-3,17-dione, mp 201°-202° C.

Workup

  1. concentrationThe mixture is then neutralized with acetic acid, concentration
  2. customprecipitated into water
  3. washwashed with water
  4. customdried
  5. customRecrystallization from acetone/hexane

Sources & evidence

ORD record
ord-21050b7463824a15bfc56e07b59e3a4c
Source dataset
uspto-grants-1986_05
Patent number
US04591585

Reaction notes

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