Ethyl formate → HCID 20073630, compound

HRID 704906Notes

Reaction equation

HRID 704906 reaction equation
Cl.[NH2:2][CH:3]([C:5]1([CH3:10])[O:9][CH2:8][CH2:7][O:6]1)[CH3:4].C[O-].[Na+].[CH:14](OCC)=[O:15]>CO>[CH:14]([NH:2][CH:3]([C:5]1([CH3:10])[O:9][CH2:8][CH2:7][O:6]1)[CH3:4])=[O:15]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 10942334Sodium MethoxideHCID 20073632HCID 20073632, compound

Product 1

HCID 20073630HCID 20073630, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(1-Aminoethyl)-2-methyl-1,3-dioxolane hydrochloride (1.3 g, 0.0078 mol) was dissolved in methanol (25 ml). Sodium methoxide (25% w/w in methanol. 1.68 g, 0.0078 mol) was added and the suspension filtered through Celite. The Celite was rinsed with methanol (25 ml) and the combined filtrates had the solvent removed by rotary evaporation (25 Torr, 40° C.). The resulting clear oil was dissolved in ethyl formate (10.36 g. 0.14 mol) and heated to reflux under nitrogen. The reflux was continued for 4 hours. The excess ethyl formate and ethanol byproduct were removed by rotary evaporation (25 Torr, 40° C.) and the resulting solid was dried in vacuo (0.5 Torr, 25° C., 16 hours). The product was

Workup

  1. filtrationthe suspension filtered through Celite
  2. washThe Celite was rinsed with methanol (25 ml)
  3. customremoved by rotary evaporation (25 Torr, 40° C.)
  4. temperatureheated
  5. temperatureto reflux under nitrogen
  6. customThe excess ethyl formate and ethanol byproduct were removed by rotary evaporation (25 Torr, 40° C.)
  7. customthe resulting solid was dried in vacuo (0.5 Torr, 25° C., 16 hours)

Sources & evidence

ORD record
ord-9160c386e03047528854ae3237ffd3ad
Source dataset
uspto-grants-1991_01
Patent number
US04988827

Reaction notes

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