Ethylene Glycol → HCID 86740969, compound

HRID 365111Notes

Reaction equation

HRID 365111 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH:9]([CH3:11])[C:8]([OH:12])=[C:7]([C:13]([O:15][CH2:16][CH3:17])=O)[CH2:6]1)=[O:4].[CH2:18]([OH:21])[CH2:19][OH:20].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[CH2:18]1[O:21][C:13]([CH:7]2[C:8](=[O:12])[CH:9]([CH3:11])[CH2:10][N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6]2)([O:15][CH2:16][CH3:17])[O:20][CH2:19]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 86740970HCID 86740970, compound

Product 1

HCID 86740969HCID 86740969, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.9 g (7.8 mmol) of (RS)-ethyl 1-methoxycarbonyl-4-hydroxy-5-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate (prepared as described in Acta Chem. Scand. B32, 327 (1978)), ethylene glycol (2.2 ml), 4-toluenesulfonic acid (0.15 g), and toluene was refluxed for 20 hours using a Dean-Stark water separator. The mixture was washed with aqueous sodium bicarbonate, dried and evaporated in vacuo. The crude product was distilled at 0.5 mm Hg, B.P. 148°-152° C. Yield 1.6 g.

Workup

  1. temperaturewas refluxed for 20 hours
  2. washThe mixture was washed with aqueous sodium bicarbonate
  3. customdried
  4. customevaporated in vacuo
  5. distillationThe crude product was distilled at 0.5 mm Hg, B.P. 148°-152° C

Sources & evidence

ORD record
ord-bcac26e7f7914c78ba5fd391c2966c5d
Source dataset
uspto-grants-1986_08
Patent number
US04608378

Reaction notes

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