N-Phenylglycine ethyl ester → ETHYL 2-PHENYL-2-(1H-PYRROL-1-YL)ACETATE

HRID 1284552Notes

Reaction equation

HRID 1284552 reaction equation
[C:1]1([NH:7][CH2:8][C:9](OCC)=O)[CH:6]=CC=CC=1.C(O[CH:17]1[CH2:21][CH2:20][CH:19]([O:22][CH2:23][CH3:24])[O:18]1)C>C(O)(=O)C>[N:7]1([CH:20]([C:21]2[CH:17]=[CH:17][CH:21]=[CH:20][CH:19]=2)[C:19]([O:22][CH2:23][CH3:24])=[O:18])[CH:1]=[CH:6][CH:9]=[CH:8]1

Participants

4

Reactant 2

HCID 75190N-Phenylglycine ethyl esterHCID 955002,5-Diethoxyoxolanato

Product 1

HCID 2798193ETHYL 2-PHENYL-2-(1H-PYRROL-1-YL)ACETATE

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

52.8 g (0.24 mole) of ethyl phenylglycinate were dissolved in 136 ml of glacial acetic acid. Thereafter 39 g (0.24 mole) of 2,5-diethoxytetrahydrofuran were added over 10-15 minutes with stirring. The mixture was heated under reflux for one hour. After this time had elapsed, the mixture was allowed to cool and the major portion of the acetic acid was drawn off under reduced pressure. Finally, the residue was distilled under vacuum and the fraction distilling out at 115°-118° C. at 0.2 mm Hg was collected. The product obtained was first a colourless oil which crystallised on cooling, adopting a waxy aspect and weighing 46.5 g (70%). M.p. 51°-53° C. Centesimal composition: 73.31% C.; 6.08% N; 6.53% H. The IR spectrum in 0.5% KBr is illustrated in FIG. 1.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for one hour
  3. temperatureto cool
  4. distillationFinally, the residue was distilled under vacuum
  5. distillationthe fraction distilling out at 115°-118° C. at 0.2 mm Hg
  6. customwas collected
  7. customThe product obtained
  8. customcrystallised
  9. temperatureon cooling

Sources & evidence

ORD record
ord-b0e828e64f3647f58539f85402a7bedf
Source dataset
uspto-grants-1986_01
Patent number
US04563477

Reaction notes

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