Water → 3beta-Acetoxy-1alpha-benzoyloxypregna-5,7-diene-20-carbaldehyde

HRID 1196382Notes

Reaction equation

HRID 1196382 reaction equation
[O:1]1CCO[CH:2]1[CH:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15]([CH2:16][C@@H:17]([O:36][C:37](=[O:39])[CH3:38])[CH2:18][C@@H:19]2[O:27][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:14][CH:13]=3)[CH2:10][CH2:9]1)[CH3:7].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1>[C:37]([O:36][C@H:17]1[CH2:18][C@H:19]([O:27][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C@@:20]2([CH3:21])[C:15](=[CH:14][CH:13]=[C:12]3[C@@H:22]2[CH2:23][CH2:24][C@@:25]2([CH3:26])[C@H:11]3[CH2:10][CH2:9][C@@H:8]2[CH:6]([CH:2]=[O:1])[CH3:7])[CH2:16]1)(=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 6785298420-(1,3-Dioxolan-2yl)-3beta-acetoxy-1alpha-benzoyloxypregna-5,7-diene

Product 1

HCID 867458313beta-Acetoxy-1alpha-benzoyloxypregna-5,7-diene-20-carbaldehydeYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

In 5 ml of tetrahydrofuran was dissolved 100 mg of 20-(1,3-dioxolan-2-yl)-3β-acetoxy-1α-benzoyloxypregna-5,7-diene, followed by addition of 1 ml of water and 10 mg of p-toluenesulfonic acid. The mixture was stirred in an atmosphere of argon gas at 50° C. for 3 hours. The reaction mixture was then worked up in the same manner as Example 156 to give 45 mg of 3β-acetoxy-1α-benzoyloxypregna-5,7-diene-20-carbaldehyde showing the following physical properties.

Sources & evidence

ORD record
ord-e77b4d54658646d6978a870b5dd1869a
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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