Ethylene Glycol → HCID 86743317, compound

HRID 1723012Notes

Reaction equation

HRID 1723012 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:11][CH2:10][CH:9]([C:12]([O:14][CH2:15][CH3:16])=O)[C:8](=[O:17])[CH2:7][CH2:6]1)=[O:4].[CH2:18]([OH:21])[CH2:19][OH:20].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O>[CH2:18]1[O:21][C:12]([CH:9]2[CH2:10][CH2:11][N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7][C:8]2=[O:17])([O:14][CH2:15][CH3:16])[O:20][CH2:19]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 14515716HCID 14515716, compound

Product 1

HCID 86743317HCID 86743317, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A mixture of ethyl 1-methoxycarbonyl-4-oxoperhydroazepine-5-carboxylate (VI; cf: Krogsgaard-Larsen, et al., Eur. J. Med. Chem.. 14 (1979) pp. 157-164) (26.9 g; 0.11 mol), ehtylene glycol (30.7 mL; 0.55 mol), 4-toluenesulphonic acid hydrate (2.11 g; 11 mmol), and toluene (200 mL) was refluxed in a Dean-Stark water separator for 4 h. Upon addition of toluene (200 mL) the reaction mixture was washed with a saturated solution of sodium bicarbonate (50 mL), dried (K2CO3) and evaporated to give crude (V), which was used without further purification as starting material for the synthesis of (IV).

Workup

  1. washwas washed with a saturated solution of sodium bicarbonate (50 mL)
  2. dry with materialdried (K2CO3)
  3. customevaporated

Sources & evidence

ORD record
ord-8d7912b522404b039876f7626f142c95
Source dataset
uspto-grants-1989_08
Patent number
US04859666

Reaction notes

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