Diethyl Ether → HCID 57274174, compound

HRID 1196308Notes

Reaction equation

HRID 1196308 reaction equation
[O:1]1[C@H:3]2[C@@H:4]([OH:24])[CH:5]=[C:6]3[C@:20]([CH3:21])([C@@H:2]12)[C@@H:19]1[C@H:9]([C@H:10]2[C@:16]([CH3:22])([CH2:17][CH2:18]1)[C@@H:13]([CH2:14][CH3:15])[CH2:12][CH2:11]2)[C@H:8]([OH:23])[CH2:7]3.CCCCCC.C(OCC)C.C(Cl)Cl>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>[O:1]1[C@H:3]2[C:4](=[O:24])[CH:5]=[C:6]3[C@:20]([CH3:21])([C@@H:2]12)[C@@H:19]1[C@H:9]([C@H:10]2[C@:16]([CH3:22])([CH2:17][CH2:18]1)[C@@H:13]([CH2:14][CH3:15])[CH2:12][CH2:11]2)[C@H:8]([OH:23])[CH2:7]3

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 8058HexaneHCID 22843882HCID 22843882, compound

Product 1

HCID 57274174HCID 57274174, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

Thus, alcoholysis of compound (III) with a lower alcohol, such as methanol, ethanol, etc., in the presence of a basic compound, such as anhydrous potassium carbonate, anhydrous sodium carbonate, etc., at a temperature of about 0° to 30° C. yields an 1α,2α-epoxypregn-4-ene-3β,7α-diol derivative of general formula (IV). This 1α,2α-epoxypregn-4-ene- 3α,7α-diol derivative (IV) is oxidized with manganese dioxide in a solvent, such as hexane, diethyl ether, methylene chloride, chloroform, etc., at room temperature to give an 1α,2α-epoxy-7a-hydroxypregn-4-en-3-one derivative of general formula (V) and finally this 1α,2α-epoxy-7α-hydroxypregn-4-en-3-one derivative is subjected to dehydration reaction in t-butyl alcohol in the presence of potassium t-butoxide at room temperature to give the compound (I-2-2). The compound (I-2-2) thus obtained can be subjected to said 6α,7α-epoxidation to compound (I-2-3) and to the reduction to compound (I-6-1) which will be described hereinafter.

Sources & evidence

ORD record
ord-065542fef1d84fedba39560342deb6fb
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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