HCID 86736737, compound → HCID 22809505, compound

HRID 1448017Notes

Reaction equation

HRID 1448017 reaction equation
C(O)(=O)C.C(O)(=O)C.[OH:9][C@@H:10]1[CH2:35][CH2:34][C@@:33]2([CH3:36])[C@H:12]([C@@H:13]([OH:38])[CH2:14][C@@H:15]3[C@@H:32]2[CH2:31][CH2:30][C@@:29]2([CH3:37])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:28])[CH2:21][CH2:22][C:23](=[O:27])[CH:24]([CH3:26])[CH3:25])[CH2:11]1>[OH-].[K+].CO>[OH:9][C@@H:10]1[CH2:35][CH2:34][C@@:33]2([CH3:36])[C@H:12]([C@@H:13]([OH:38])[CH2:14][C@@H:15]3[C@@H:32]2[CH2:31][CH2:30][C@@:29]2([CH3:37])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:28])[CH2:21][CH2:22][C:23](=[O:27])[CH:24]([CH3:26])[CH3:25])[CH2:11]1

Participants

4

Reactant 1

HCID 86736737HCID 86736737, compound

Product 1

HCID 22809505HCID 22809505, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

3α,6α-Dihydroxy-5β-cholestan-24-one diacetate prepared in Example 2 was dissolved in a solution of potassium hydroxide (11 g) in methanol (200 ml), and the solution was stirred at room temperature for 3 hours. The reaction mixture was concentrated into about 50 ml in volume. Water was added to the concentrate and the separated oil was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel to give 3 g of 3α,6α-dihydroxy-5β-cholestan-24-one having a melting point of 180°-181° C. after recrystallization from ethyl acetate.

Workup

  1. concentrationThe reaction mixture was concentrated into about 50 ml in volume
  2. additionWater was added to the
  3. concentrationconcentrate
  4. extractionthe separated oil was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-2ac2f6f917c646f5a7e072037ae79f42
Source dataset
uspto-grants-1979_12
Patent number
US04179452

Reaction notes

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