Ethylene Glycol → HCID 22789157, compound

HRID 1606356Notes

Reaction equation

HRID 1606356 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C@H:5]1[CH2:24][C@@:23]2([CH3:25])[C@@H:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:22]2[C:21](=[O:26])[CH2:20][C@@:19]2([CH3:27])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[C:16](=[O:18])[CH3:17])[CH2:7][C@@H:6]1[OH:28].[CH2:29](O)[CH2:30][OH:31].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Cl:1][CH2:2][CH2:3][O:4][C@H:5]1[CH2:24][C@@:23]2([CH3:25])[C@@H:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:22]2[C:21](=[O:26])[CH2:20][C@@:19]2([CH3:27])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[C:16]2([O:31][CH2:30][CH2:29][O:18]2)[CH3:17])[CH2:7][C@@H:6]1[OH:28]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 22789153HCID 22789153, compound

Product 1

HCID 22789157HCID 22789157, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2β-(2'-Chloroethoxy)-3α-hydroxy-5α-pregnane-11,20-dione (600 mg.) was dissolved in benzene (50 ml.), ethylene glycol (5 ml.) and toluene-p-sulphonic acid (2 mg.) added, and the vigorously stirred mixture refluxed under a Dean and Stark head for 20 hours. The cooled mixture was washed with sodium bicarbonate solution (5 ml.), water (2 × 100 ml.) and dried over anhydrous sodium sulphate. The dried solution was evaporated in vacuo to give the title compound (605 mg.) as a pale yellow foam, [α]D + 47.2° (c 1.11).

Workup

  1. temperaturethe vigorously stirred mixture refluxed under a Dean and Stark head for 20 hours
  2. washThe cooled mixture was washed with sodium bicarbonate solution (5 ml.), water (2 × 100 ml.)
  3. dry with materialdried over anhydrous sodium sulphate
  4. customThe dried solution was evaporated in vacuo

Sources & evidence

ORD record
ord-4d026397dc8a461e8c8bdef036dcc235
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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