ChemicalBook CAS DataBase List 1,5-DIHYDRO-PYRROL-2-ONE

1,5-DIHYDRO-PYRROL-2-ONE synthesis

5synthesis methods

Product Name:1,5-DIHYDRO-PYRROL-2-ONE
CAS Number:4031-15-6
Molecular formula:C4H5NO
Molecular Weight:83.09

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Yield:4031-15-6 44%

Reaction Conditions:

with tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride;titanium(IV) isopropylate in toluene at 80; for 32 h;Catalytic behavior;Inert atmosphere;Reagent/catalyst;Time;

Steps:

Ring-closing metathesis reaction of diene amides4-6 a-f (General method).
General procedure: Method I (Grubbs I catalyst). The Grubbs I catalyst (5-10 mol %) was added to adegassed homogeneous solution of diene amides 4a, 5a(1 mmol) in dry PhMe (5 ml) under inert atmosphere, andreaction mixture was heated at 80°C for 32 h. The reactionmixture was concentrated and purified by column chromatography,yielding a small amount of required lactamsalong with major part of starting diene amides.Method II (Grubbs II catalyst). Solution of diene amides4-6 a-f (1 mmol) in dry PhMe (5 ml) was degassed well,and Grubbs II catalyst (5-10 mol %) was added under inertatmosphere. The resulting mixture was stirred at 80°C for14 or 32 h. The reaction mixture was concentrated andpurified on silica gel column using EtOAc-petroleum etheras eluent.1,5-Dihydro-2H-pyrrol-2-one (7a).10 Colorless oil.IR spectrum, ν, cm-1: 3437, 2979, 1689, 1450, 1293, 1178.1H NMR spectrum, δ, ppm: 4.11-4.17 (2H, m, CH2); 6.14-6.20 (1H, m, CH); 7.11-7.16 (1H, m, CH); 8.01 (1H, br. s,NH). 13C NMR spectrum, δ, ppm: 51.64; 114.7; 137.5;176.2. Mass spectrum, m/z (Irel, %): 83 [M]+ (100), 61 (45),57 (39). Found, m/z: 83.0389 [M]+. C4H5NO. Calculated,m/z: 83.0365.

References:

Gondal, Humaira Yasmeen;Buisson, Didier [Chemistry of Heterocyclic Compounds,2016,vol. 52,# 3,p. 183 - 191][Khim. Geterotsikl. Soedin.,2016,vol. 52,# 3,p. 183 - 191,9]

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109-97-7 Synthesis