HCID 13178927, compound → HCID 13178929, compound

HRID 596567Notes

Reaction equation

HRID 596567 reaction equation
[OH:1][C@@H:2]1[C@@:26]2([CH3:27])[C:6](=[CH:7][CH2:8][C@@H:9]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:28])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:5][C@@H:4]([O:29][C:30](=[O:32])[CH3:31])[C@@H:3]1[OH:33]>C(OC(=O)C)(=O)C.N1C=CC=CC=1>[C:2]([O:1][C@@H:2]1[C@@:26]2([CH3:27])[C:6](=[CH:7][CH2:8][C@@H:9]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:28])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:19])[CH3:20])[CH2:5][C@@H:4]([O:29][C:30](=[O:32])[CH3:31])[C@@H:3]1[O:33][C:4](=[O:29])[CH3:5])(=[O:1])[CH3:3]

Participants

4

Reactant 1

HCID 13178927HCID 13178927, compound

Product 1

HCID 13178929HCID 13178929, compoundYield 147.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 7918Acetic AnhydrideSolvent

Procedure

1α,2α-Dihydroxy-3β-acetoxy-cholesta-5-ene (264 mg) was dissolved in a mixture of acetic anhydride (20 ml) and pyridine (2 ml) and the solution was heated on a boiling water bath for 2 hours to remove acetic anhydride. To the solution was added ice-water and the precipitated crystals were recovered by filtration. Recrystallization of the crystals from methanol yielded 1α,2α,3β-triacetoxycholesta-5-ene (230 mg) having a melting point between 109 and 110° C.

Workup

  1. temperaturethe solution was heated on a boiling water bath for 2 hours
  2. customto remove acetic anhydride
  3. additionTo the solution was added ice-water
  4. filtrationthe precipitated crystals were recovered by filtration
  5. customRecrystallization of the crystals from methanol

Sources & evidence

ORD record
ord-5c9ad7ae306a4956b3c4cedf17daf179
Source dataset
uspto-grants-1977_03
Patent number
US04011250

Reaction notes

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