p-Toluenesulfonic acid → 21-Acetoxy-17alpha-hydroxy-6-methylene-4-pregnene-3,20-dione

HRID 2059169Notes

Reaction equation

HRID 2059169 reaction equation
[C:1]([O:4][CH2:5][C:6](=[O:28])[C@:7]1([OH:27])[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([CH2:22][CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:26])[CH2:17][CH2:18]2)[CH2:13][CH2:12]3)[CH2:9][CH2:8]1)(=[O:3])[CH3:2].[C:29]1(C)C=CC(S(O)(=O)=O)=CC=1>>[C:1]([O:4][CH2:5][C:6](=[O:28])[C@:7]1([OH:27])[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([CH2:22][CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:26])[CH2:17][CH2:18]2)[C:13](=[CH2:29])[CH2:12]3)[CH2:9][CH2:8]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 10181611-Deoxycortisol 21-acetate

Product 1

HCID 1295179021-Acetoxy-17alpha-hydroxy-6-methylene-4-pregnene-3,20-dioneYield 66%

Procedure

1.0 g of 21-acetoxy-17α-hydroxy-4-pregnene-3,20-dione is reacted, using 2.0 g of p-toluenesulfonic acid, analogously to Example 42 and purified, thus obtaining 680 mg of 21-acetoxy-17α-hydroxy-6-methylene-4-pregnene-3,20-dione, mp 194°-196° C.

Workup

  1. customanalogously to Example 42 and purified

Sources & evidence

ORD record
ord-a95dec3c50e7486894b97a753c830196
Source dataset
uspto-grants-1982_03
Patent number
US04322349

Reaction notes

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