Water → 3beta-(2-Tosyioxyethylthio)-17beta-(3-furyl)-5beta-androstan-14beta-ol

HRID 233647Notes

Reaction equation

HRID 233647 reaction equation
[OH:1][CH2:2][CH2:3][S:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@:11]3([OH:29])[CH2:12][CH2:13][C@@H:14]2[C:24]2[CH:28]=[CH:27][O:26][CH:25]=2)[CH2:6]1.[S:30](Cl)([C:33]1[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=1)(=[O:32])=[O:31].O.C(OCC)(=O)C>N1C=CC=CC=1>[S:30]([O:1][CH2:2][CH2:3][S:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@:11]3([OH:29])[CH2:12][CH2:13][C@@H:14]2[C:24]2[CH:28]=[CH:27][O:26][CH:25]=2)[CH2:6]1)([C:33]1[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=1)(=[O:32])=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 70044279HCID 70044279, compound

Product 1

HCID 867487853beta-(2-Tosyioxyethylthio)-17beta-(3-furyl)-5beta-androstan-14beta-olYield 97.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 0.90 g of 3β-(2-hydroxyethylthio)-17β-(3-furyl)-5β-androstan-14β-ol, in 9 ml of dry pyridine, 0.64 g of tosylchloride were added. After 5 hrs 10 ml of water and 50 ml of ethyl acetate were added. The organic phase was washed with water, dried over anhydrous sodium sulfate to give 1.2 g of 3β-(2-tosyioxyethylthio)-17β-(3-furyl)-5β-androstan-14β-ol as a colourless oil.

Workup

  1. washThe organic phase was washed with water
  2. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-3a1e2f52ffd249fcb1c22715399d7ab5
Source dataset
uspto-grants-1997_01
Patent number
US05593982

Reaction notes

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