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Ethyl formate → Potassium 2-ethoxycarbonyl-2-(1-ethoxy-ethylideneamino)-ethenolate

HRID 602820
Notes
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Reaction equation

HRID 602820 reaction equation
[O-]CC.[K+:4].[CH:5]([O:7][CH2:8][CH3:9])=[O:6].C([O:12][C:13](=O)[CH2:14][N:15]=[C:16]([O:18][CH2:19][CH3:20])[CH3:17])C>C(OCC)C.CCO>[CH2:8]([O:7][C:5]([C:14]([N:15]=[C:16]([O:18][CH2:19][CH3:20])[CH3:17])=[CH:13][O-:12])=[O:6])[CH3:9].[K+:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8025Ethyl formateHCID 295983Ethyl 2-(1-ethoxyethylideneamino)acetateHCID 23670592Potassium ethoxide

Product 1

HCID 86600794Potassium 2-ethoxycarbonyl-2-(1-ethoxy-ethylideneamino)-ethenolateYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×
HCID 3283
Diethyl Ether
Solvent
3×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 3.222 g (36 mmol, 1.05 eq) of potassium ethoxide in 30 mL diethyl ether and 5 mL EtOH at 0° C., a solution of 3.849 g (52 mmol, 1.5 eq) ethyl formate and 6 g (35 mmol) (1-ethoxy-ethylideneamino)-acetic acid ethyl ester in 30 mL diethyl ether and 5 mL EtOH is then slowly added. The reaction mixture is stirred for one hour at 0° C. After addition of 40 mL diethyl ether, the reaction mixture was stirred at RT overnight. The reaction mixture was filtered and the obtained solid was washed with diethyl ether and dried under vaccum to yielded 5 g (60%) of potassium 2-ethoxycarbonyl-2-(1-ethoxy-ethylideneamino)-ethenolate as an orange solids.

Workup

  1. stirringthe reaction mixture was stirred at RT overnight
  2. filtrationThe reaction mixture was filtered
  3. washthe obtained solid was washed with diethyl ether
  4. customdried under vaccum

Sources & evidence

ORD record
ord-7604398ec82245c4bb68a8a1f10f6e79
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07906546B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes