Ethylene Glycol → Ethyl 1,4-dioxa-8-azaspiro[4.6]undecane-8-carboxylate

HRID 968485Notes

Reaction equation

HRID 968485 reaction equation
[O:1]=[C:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:3]1.[CH2:14](O)[CH2:15][OH:16]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:16]1[C:2]2([CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:3]2)[O:1][CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 126660861-Carbethoxyazepan-4-one

Product 1

HCID 69282947Ethyl 1,4-dioxa-8-azaspiro[4.6]undecane-8-carboxylateYield 106.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture of ethyl hexahydro-4-oxoazepine-1-carboxylate (0.585 mol), 1,2-ethane-diol (0.585 mol) and p-toluenesulfonic acid (0.0058 mol) in toluene (800 ml) was stirred and refluxed overnight, using a water separator (10.5 ml was separated). The solvent was evaporated, yielding 142.5 g of ethyl 1,4-dioxa-8-azaspiro[4.6]undecane-8-carboxylate (intermediate 4).

Workup

  1. temperaturerefluxed overnight
  2. customa water separator (10.5 ml was separated)
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-4b57ffa914894fe2b14cd67efb4f9d05
Source dataset
uspto-grants-2007_12
Patent number
US07304052B2

Reaction notes

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