HCID 25444, compound → Cholesterol

HRID 1090068Notes

Reaction equation

HRID 1090068 reaction equation
CC(C)=O.C(OCC)C.[CH3:10][C@H:11]1[CH2:94]O[C@@:14]2(O[C@H:17]3[C@@H:19](O)[C@H:20]4[C@@H:25]5[CH2:26][CH2:27][C@H:28]6[CH2:33][C@@H:32]([O:34][C@@H]7O[C@H](CO)[C@H](O[C@@H]8O[C@H](CO)C(O)[C@H](O[C@@H]9OC[C@@H](O)[C@H](O)[C@H]9O)[C@H]8O[C@@H]8O[C@H](CO)[C@H](O)[C@H](O[C@@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@H]9O)[C@H]8O)[C@H](O)[C@H]7O)[C@H:31](O)[CH2:30][C@:29]6([CH3:89])[C@H:24]5[CH2:23][CH2:22][C@:21]4([CH3:90])[C@H:16]3[C@@H:15]2[CH3:92])[CH2:13][CH2:12]1>C(O)C>[CH3:94][CH:11]([CH2:12][CH2:13][CH2:14][C@H:15]([C@@H:16]1[C@:21]2([CH3:90])[C@H:20]([C@H:25]3[C@H:24]([CH2:23][CH2:22]2)[C@:29]2([CH3:89])[C:28]([CH2:33][C@H:32]([CH2:31][CH2:30]2)[OH:34])=[CH:27][CH2:26]3)[CH2:19][CH2:17]1)[CH3:92])[CH3:10]

Participants

4

Reactant 2

HCID 25444HCID 25444, compoundHCID 21584533Acetone diethylether

Product 1

HCID 5997Cholesterol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The whole mixture was incubated at 37° C. for 90 minutes, then the reaction was terminated by adding 1 mM of 15%-KOH (a 95% ethanol solution), next 2 mg of cholesterol was added thereto, saponified at 75° C. for 1 hour, and cholesterol was extracted with petroleum ether, the extract was concentrated to dryness. To the residue thus obtained was added with 2.5 ml of a mixture of acetone-diethyl ether (1:1) and 2.5 ml of 1%-digitonin (a 50% ethanol solution), then this solution was allowed to stand for 1 hour in cooling condition by using ice-water to precipitate cholesterol. The precipitate was washed with acetone, a mixture of acetonediethyl ether (1:1) and diethyl ether in this order, then the radioactivity of the residue was measured by using a liquid scintillation counter.

Workup

  1. customthe reaction was terminated
  2. additionby adding 1 mM of 15%-KOH (a 95% ethanol solution), next 2 mg of cholesterol
  3. additionwas added
  4. waitsaponified at 75° C. for 1 hour
  5. extractioncholesterol was extracted with petroleum ether
  6. concentrationthe extract was concentrated to dryness
  7. customTo the residue thus obtained
  8. waitto stand for 1 hour
  9. temperaturein cooling condition
  10. customto precipitate cholesterol
  11. washThe precipitate was washed with acetone
  12. additiona mixture of acetonediethyl ether (1:1) and diethyl ether in this order

Sources & evidence

ORD record
ord-db98ed722f304bf2b2800f3e47275256
Source dataset
uspto-grants-1992_01
Patent number
US05081112

Reaction notes

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