Ethylene Glycol → HCID 86738507, compound

HRID 1980055Notes

Reaction equation

HRID 1980055 reaction equation
[C:1]([CH:9]1[C:14](=[O:15])[NH:13][CH2:12][CH2:11][N:10]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23](O)[CH2:24][OH:25].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C>C1C=CC=CC=1.O>[O:15]=[C:14]1[NH:13][CH2:12][CH2:11][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:9]1[CH:1]1[O:8][CH2:23][CH2:24][O:25][C:7]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]1=2

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 90495Di-tert-butyl dicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 20437866HCID 20437866, compound

Product 1

HCID 86738507HCID 86738507, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 2.0 g (6.5 mmole) of 27d, 1.25 g (20.0 mmole) of ethyleneglycol, and 1.0 g of p-toluenesulfonic acid monohydrate is refluxed in 50 ml of benzene in a Dean-Stark apparatus until the collection of water ceases. The reaction mixture is cooled, washed with saturated NaHCO3 solution and brine, dried over MgSO4, and filtered. The filtrate is stirred with 2.2 g (10 mmole) of di-t-butyldicarbonate at reflux temperature and then concentrated to a solid residue and recrystallized from benzene/hexane to yield the title compound.

Workup

  1. temperatureThe reaction mixture is cooled
  2. washwashed with saturated NaHCO3 solution and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. temperatureat reflux temperature
  6. concentrationconcentrated to a solid residue
  7. customrecrystallized from benzene/hexane

Sources & evidence

ORD record
ord-204e1d346b0d44c08dcb58638bf2e6b5
Source dataset
uspto-grants-1984_11
Patent number
US04483988

Reaction notes

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