Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → Cholesta-5,7-diene-3,24,25-triol, (3beta,24R)-
Reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O1CCCC([O:24][C@H:25]2[CH2:51][CH2:50][C@@:49]3([CH3:52])[C:27](=[CH:28][CH:29]=[C:30]4[C@@H:48]3[CH2:47][CH2:46][C@@:45]3([CH3:53])[C@H:31]4[CH2:32][CH2:33][C@@H:34]3[C@H:35]([CH3:44])[CH2:36][CH2:37][C@@H:38]([OH:43])[C:39]([OH:42])([CH3:41])[CH3:40])[CH2:26]2)C1>C(O)C>[CH3:40][C:39]([OH:42])([C@H:38]([OH:43])[CH2:37][CH2:36][C@H:35]([C@@H:34]1[C@:45]2([CH3:53])[C@H:31]([C:30]3[C@H:48]([CH2:47][CH2:46]2)[C@:49]2([CH3:52])[C:27]([CH2:26][C@@H:25]([OH:24])[CH2:51][CH2:50]2)=[CH:28][CH:29]=3)[CH2:32][CH2:33]1)[CH3:44])[CH3:41]Participants
4
Procedure
Pyridinium p-toluenesulfonate (12.5 mg) was added to a solution of (24R)-5,7-cholestadiene-3β,24,25-triol 3-tetrahydropyranyl ether (25 mg) in 2 ml of ethanol in an argon stream under stirring, and the mixture was left to stand at room temperature for 2 days. The reaction mixture was evaporated with 40 ml of ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give 14 mg (67%) of (24R)-5,7-cholestadiene-3β,24,25-triol.
Workup
- waitthe mixture was left
- customThe reaction mixture was evaporated with 40 ml of ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-0a6a5c722d1a495c9ef67f489c7f9b60
- Source dataset
- uspto-grants-1982_08
- Patent number
- US04344888
Reaction notes
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