Ethylene Glycol → HCID 70583481, compound

HRID 1701439Notes

Reaction equation

HRID 1701439 reaction equation
[CH3:1][C:2](=[O:23])[C@@H:3]1[C@:20]2([CH3:21])[C@H:6]([C@H:7]3[C@H:17]([C:18](=[O:22])[CH2:19]2)[C@:15]2([CH3:16])[C@H:10]([CH2:11][CH:12]=[CH:13][CH2:14]2)[CH2:9][CH2:8]3)[CH2:5][CH2:4]1.[CH2:24](O)[CH2:25][OH:26].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:24]1[CH2:25][O:26][C:2]([C@@H:3]2[C@:20]3([CH3:21])[C@H:6]([C@H:7]4[C@H:17]([C:18](=[O:22])[CH2:19]3)[C@:15]3([CH3:16])[C@H:10]([CH2:11][CH:12]=[CH:13][CH2:14]3)[CH2:9][CH2:8]4)[CH2:5][CH2:4]2)([CH3:1])[O:23]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 705865025alpha-Pregn-2-ene-11,20-dione

Product 1

HCID 70583481HCID 70583481, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5α-Pregn-2-ene-11,20-dione (10 g) in benzene (300 ml) was treated with ethylene glycol (30 ml) and toluene-4-sulphonic acid (100 mg), and the vigorously stirred mixture was refluxed through a Dean and Stark separator for 8 hours. The reaction mixture was partitioned between ether/ethyl acetate and dilute sodium bicarbonate solution. The organic layer was washed with water (3 times), dried over sodium sulphate and evaporated to a solidifying oil which was triturated with petrol to give title compound (9.42 g) as an off-white solid, m.p. 130°-135°, [α]D +111°.

Workup

  1. temperaturethe vigorously stirred mixture was refluxed through a Dean and Stark
  2. customThe reaction mixture was partitioned between ether/ethyl acetate and dilute sodium bicarbonate solution
  3. washThe organic layer was washed with water (3 times)
  4. dry with materialdried over sodium sulphate
  5. customevaporated to a solidifying oil which
  6. customwas triturated with petrol

Sources & evidence

ORD record
ord-c56d0dcd34d844cfa3acc0c01d1c7412
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

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