2-Chloroethanol → HCID 54115112, compound

HRID 440721Notes

Reaction equation

HRID 440721 reaction equation
[SH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:21])[CH2:3]1.Cl[CH2:23][CH2:24][OH:25].[H-].[Na+]>O1CCCC1.O>[OH:25][CH2:24][CH2:23][S:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:21])[CH2:3]1

Participants

6

Reactant 3

HCID 342-ChloroethanolHCID 24758Sodium hydrideHCID 2376443-Sulfanylandrost-5-en-17-one

Product 1

HCID 54115112HCID 54115112, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.0 g of 3β-mercapto-androst-5-en-17-one (Swann D. A. and Turnbull J. H., Tetrahedron, 1966, 22, 231) and 0.33 ml of 2-chloroethanol in 5.0 ml of tetrahydrofuran under nitrogen atmosphere at room temperature, 0.030 g of sodium hydride (60% dispersion in mineral oil) were added. The reaction mixture was stirred for 3 hrs, diluted with water and extracted with ethyl acetate; the organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using methylene chloride/methanol/30% ammonia solution 95/5/1 as eluant to give 1.2 g of 3β-(2-hydroxyethylthio)-androst-5-en-17-one.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. customevaporated to dryness under reduced pressure
  4. customThe crude product was purified by flash-chromatography (SiO2)

Sources & evidence

ORD record
ord-586fd431d3ed4bcb9914c3bc1ccf5fd7
Source dataset
uspto-grants-1996_05
Patent number
US05521167

Reaction notes

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