Ethylene Glycol → HCID 12796495, compound

HRID 2049477Notes

Reaction equation

HRID 2049477 reaction equation
[CH2:1]([O:3][C@H:4]1[CH2:21][C@@:20]2([CH3:22])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[C:18](=[O:23])[CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:24])[CH2:6][C@@H:5]1[OH:25])[CH3:2].[CH2:26](O)[CH2:27][OH:28].C([O-])([O-])OCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[CH2:26]1[CH2:27][O:28][C:14]2([CH2:13][CH2:12][C@H:11]3[C@H:10]4[C@H:19]([C:18](=[O:23])[CH2:17][C@:15]23[CH3:16])[C@:20]2([CH3:22])[C@H:7]([CH2:6][C@H:5]([OH:25])[C@@H:4]([O:3][CH2:1][CH3:2])[CH2:21]2)[CH2:8][CH2:9]4)[O:24]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 12796459HCID 12796459, compoundHCID 53630039Ethylorthoformate

Product 1

HCID 12796495HCID 12796495, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2β-ethoxy-3α-hydroxy-5α-androstane-11,17-dione (8 g) in chloroform (80 ml) containing ethylene glycol (13 ml), ethyl orthoformate (8.3 ml) and p-toluene sulphonic acid (160 mg) was kept at room temperature overnight. The reaction mixture was washed with sodium bicarbonate solution and water, dried (Na2SO4) and evaporated in vacuo. Purification of the residual froth (8.6 g) by preparative thin layer chromatography over silica (acetone-petroleum ether 3:7) and crystallization from ethyl acetate-petroleum ether afforded the title compound m.p. 142°-145°, [α]D +18.2°.

Workup

  1. washThe reaction mixture was washed with sodium bicarbonate solution and water
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo
  4. customPurification of the residual froth (8.6 g) by preparative thin layer chromatography
  5. customover silica (acetone-petroleum ether 3:7) and crystallization from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-f2d26b09595c4e63b10e958f87d6b14f
Source dataset
uspto-grants-1980_04
Patent number
US04197296

Reaction notes

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