HCID 86736737, compound → HCID 22809505, compound

HRID 28087Notes

Reaction equation

HRID 28087 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 purified by chromatography on silica gel. Elution with chloroform gave 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 purified by chromatography on silica gel
  9. washElution with chloroform

Sources & evidence

ORD record
ord-e33d5b34aacb44f1a64e63b9cd3a6d1e
Source dataset
uspto-grants-1980_09
Patent number
US04225524

Reaction notes

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