Ethanol → 3-Ethoxy-1alpha-methyl-3,5-androstadien-17beta,19-diol dipropionate

HRID 1834964Notes

Reaction equation

HRID 1834964 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][CH3:3].[C:6]([OH:10])(=O)[CH2:7][CH3:8].O[C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:29]([CH2:30][CH2:31][C@:13]12[CH3:14])[C@:26]1([CH2:27][OH:28])[C:21](=[CH:22][C:23](=[O:33])[CH2:24][C@@H:25]1[CH3:32])[CH2:20][CH2:19]3.[CH2:34](OC(OCC)OCC)[CH3:35].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)C>O1CCCC1.N1C=CC=CC=1>[C:1]([O:5][C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:29]([CH2:30][CH2:31][C@:13]12[CH3:14])[C@:26]1([CH2:27][O:28][C:6](=[O:10])[CH2:7][CH3:8])[C:21]([CH:22]=[C:23]([O:33][CH2:34][CH3:35])[CH2:24][C@@H:25]1[CH3:32])=[CH:20][CH2:19]3)(=[O:4])[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 8673472917beta,19-Dihydroxy-1alpha-methyl-4-androsten-3-one dipropionate

Product 1

HCID 706145673-Ethoxy-1alpha-methyl-3,5-androstadien-17beta,19-diol dipropionate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 17β,19-dihydroxy-1α-methyl-4-androsten3-one dipropionate, triethylorthoformate, p-toluenesulfonic acid and ethanol in tetrahydrofuran is stirred at room temperature for about 2 hours. The reaction mixture is poured onto ice water containing a few drops of pyridine and stirred well. The solid which forms is filtered and crystallized from ethanol to yield pure 3-ethoxy-1α-methyl-3,5-androstadiene-17β,19-diol dipropionate.

Workup

  1. filtrationThe solid which forms is filtered
  2. customcrystallized from ethanol

Sources & evidence

ORD record
ord-1d08688b2d604ab4930ee0346a1fa7f0
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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