Ethylene Glycol → HCID 22789161, compound

HRID 1606358Notes

Reaction equation

HRID 1606358 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C@H:6]1[CH2:25][C@@:24]2([CH3:26])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:23]2[C:22](=[O:27])[CH2:21][C@@:20]2([CH3:28])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:17](=[O:19])[CH3:18])[CH2:8][C@@H:7]1[OH:29].[CH2:30](O)[CH2:31][OH:32].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CCOCC.C1C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C@H:6]1[CH2:25][C@@:24]2([CH3:26])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:23]2[C:22](=[O:27])[CH2:21][C@@:20]2([CH3:28])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:17]2([O:32][CH2:31][CH2:30][O:19]2)[CH3:18])[CH2:8][C@@H:7]1[OH:29]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 22789162HCID 22789162, compound

Product 1

HCID 22789161HCID 22789161, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

2β-(3'-Chloropropoxy)-3α-hydroxy-5α-pregnane-11,20-dione (470 mg.) was added to a mixture of ethylene glycol (4 ml.), toluene-p-sulphonic acid (3 mg.) and benzene (50 ml.). The vigorously stirred mixture was refluxed under a Dean and Stark head for 17 hours. The cooled mixture was neutralised with sodium bicarbonate solution, ether (50 ml.) added and the organic mixture was washed with water (250 ml.). The organic solution was dried over anhydrous sodium sulphate and evaporated to give the title compound (520 mg.) as a white foam, [α]D + 37.5° (c 1.03).

Workup

  1. temperatureThe vigorously stirred mixture was refluxed under a Dean and Stark head for 17 hours
  2. additionadded
  3. washthe organic mixture was washed with water (250 ml.)
  4. dry with materialThe organic solution was dried over anhydrous sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-1d223e4f54a741e5a844642d67277097
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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