Ethylene Glycol → HCID 57036002, compound

HRID 1722667Notes

Reaction equation

HRID 1722667 reaction equation
[CH2:1]([C@H:5]1[C@H:9]([CH2:10][CH2:11][C:12](=[O:18])[CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[O:8][C:7](=[O:19])[NH:6]1)[CH:2]([CH3:4])[CH3:3].[CH2:20](O)[CH2:21][OH:22].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:21]1[O:22][C:7]2([NH:6][C@@H:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C@H:9]([CH2:10][CH2:11][C:12](=[O:18])[CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[O:8]2)[O:19][CH2:20]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 13891056HCID 13891056, compound

Product 1

HCID 57036002HCID 57036002, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of the product from Example 27 (2.5 g, 9.3 mmol), ethylene glycol (7.5 mL) and p-toluenesulfonic acid (60 mg) in toluene (100 mL) was heated at reflux with a Dean-Stark trap for 8 hours. The cooled mixture was washed with aqueous NaHCO3 and dried over MgSO4. Evaporation of the solvent gave a residue which was flash chromatographed on silica gel eluting with 65/35 hexane-ethyl acetate to give 2.3 g (79%) of product. NMR (300 MHz, CDCl3, ppm): 0.85-0.95 (4d, 12H), 3.5 (m, 1H), 3.95 (s, 4H), 4.15 (m, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux with a Dean-Stark trap for 8 hours
  3. washThe cooled mixture was washed with aqueous NaHCO3
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent
  6. customgave a residue which
  7. customchromatographed on silica gel eluting with 65/35 hexane-ethyl acetate

Sources & evidence

ORD record
ord-7855a8d0156a40a889eeae5202470baf
Source dataset
uspto-grants-1989_08
Patent number
US04857507

Reaction notes

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