Ethylene Glycol → HCID 21459585, compound

HRID 1941020Notes

Reaction equation

HRID 1941020 reaction equation
[CH3:1][C:2]12[CH2:29][CH:5]([C:6]3([CH3:28])[C:10]1([CH3:11])[C:9]1[CH:12]=[C:13]([C:16]([C:18]4[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=4)=[O:17])[CH:14]=[CH:15][C:8]=1[O:7]3)[CH2:4][CH2:3]2.[CH2:30](O)[CH2:31][OH:32].CC1C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[CH3:1][C:2]12[CH2:29][CH:5]([C:6]3([CH3:28])[C:10]1([CH3:11])[C:9]1[CH:12]=[C:13]([C:16]4([C:18]5[CH:19]=[CH:20][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:26][CH:27]=5)[O:32][CH2:31][CH2:30][O:17]4)[CH:14]=[CH:15][C:8]=1[O:7]3)[CH2:4][CH2:3]2

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 21459573HCID 21459573, compound

Product 1

HCID 21459585HCID 21459585, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2 g (5.12 mmol) of the ketone obtained in Example 8, in 20 ml of benzene, were treated with 0.5 ml of ethylene glycol and 10 mg of TsOH. The reaction mixture was heated at reflux for 24 hours and was then neutralized with a saturated sodium bicarbonate solution. After extraction with ethyl ether, the organic phase was washed with water, dried over magnesium sulfate, filtered and evaporated to yield, after chromatography on silica in a hexane/EtOAc (90/10) mixture and triturating in hexane, 910 mg (41%) of the expected compound, melting at 136°-137° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 24 hours
  3. extractionAfter extraction with ethyl ether
  4. washthe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto yield
  9. customafter chromatography on silica in a hexane/EtOAc (90/10) mixture and triturating in hexane

Sources & evidence

ORD record
ord-c2063b01413c46a39337f710a375eff1
Source dataset
uspto-grants-1997_12
Patent number
US05702710

Reaction notes

Loading…