Sodium Methoxide → 1alpha-Hydroxy-3beta-(methoxymethyl)oxypregna-5,7-diene-20-carbaldehyde

HRID 1196389Notes

Reaction equation

HRID 1196389 reaction equation
C([O:4][C@@H:5]1[C@@:25]2([CH3:26])[C:9](=[CH:10][CH:11]=[C:12]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:27])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[CH:17]([CH:19]=[O:20])[CH3:18])[CH2:8][C@@H:7]([O:28][CH2:29][O:30][CH3:31])[CH2:6]1)(=O)C.C[O-].[Na+]>CO>[OH:4][C@@H:5]1[C@@:25]2([CH3:26])[C:9](=[CH:10][CH:11]=[C:12]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:27])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[CH:17]([CH:19]=[O:20])[CH3:18])[CH2:8][C@@H:7]([O:28][CH2:29][O:30][CH3:31])[CH2:6]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 228438981alpha-Acetoxy-3beta-(methoxymethyl)oxypregna-5,7-diene-20carbaldehyde

Product 1

HCID 867458361alpha-Hydroxy-3beta-(methoxymethyl)oxypregna-5,7-diene-20-carbaldehydeYield 88.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 10 ml of methanol was dissolved 100 mg of 1α-acetoxy-3β-(methoxymethyl)oxypregna-5,7-diene-20-carbaldehyde, followed by addition of 50 mg of sodium methoxide. The mixture was stirred in an atmosphere of argon gas for 2 hours. The reaction mixture was then worked up in the same manner as Example 164 to give 80 mg of 1α-hydroxy-3β-(methoxymethyl)oxypregna-5,7-diene-20-carbaldehyde showing the following physical properties.

Sources & evidence

ORD record
ord-6607f98e4c1c408097f2c05fd7d23268
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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