ChemicalBook CAS DataBase List 5,5-DIMETHYL-1-PYRROLINE N-OXIDE

5,5-DIMETHYL-1-PYRROLINE N-OXIDE synthesis

3synthesis methods

Product Name:5,5-DIMETHYL-1-PYRROLINE N-OXIDE
CAS Number:3317-61-1
Molecular formula:C6H11NO
Molecular Weight:113.16

To a three-necked round bottom flask equipped with a condenser, addition funnel, thermometer, and mechanical stirrer and containing 300 ml. 95% ethanol precooled to 2°C is added, all at once, 14.5 g (0.1 mole) 4-methyl-4-nitropentanol, and 13.1 g (1.2 mole) zinc dust. With rapid agitation, the glacial acetic acid (24.0 g, 0.4 mole) is added dropwise over a 1-hr period while maintaining the reaction temperature below 15°C. The mixture is stirred vigorously for 2 hr and then stored in the refrigerator for 2 days, at approximately 1°C. Then the zinc acetate is filtered and rinsed with 100 ml of ethanol. The combined ethanol factions are rotoevapo-rated to give the crude nitrone. The crude nitrone is dissolved in a 200 ml portion of dichloromethane and the latter washed two times with saturated sodium bicarbonate solution. The organic layer is dried over sodium sulfate and the solvent rotoevaporated, to give 10.7 (94% yield) of the crude nitrone. The product was purified by double distillation (b.p. 53°C, 0.1 Torr), to give 6.8 g (60%) of the pure nitrone as a white hygroscopic solid. The H¹ NMR (400 MH CDC1₃, Me₄Si) is 6.80 (t, 2H, methylene bound to quaternary C, J = 7.2Hg), 1.43 (s, 6H, methyl), C¹³NMr (100 MH2, CDC13, Me₄ Si) 5=132.4 (Vinyl), 73.5 (quaternary), 34.1 (Allyl), 25.3 (methylene bound to quaternary C), 24.4 (methyls).
Preparation of 5,5-dimethyl-l-pyrroline-N-oxide

Preparation of 5,5-dimethyl-l-pyrroline-N-oxide

57620-49-2
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3317-61-1
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Yield:-

Steps:

Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid
2.1: ammonium chloride; zinc / tetrahydrofuran; water / 2 h / 3 - 10 °C
2.2: 2 h / 70 °C

References:

Khoroshunova, Yulia V.;Morozov, Denis A.;Taratayko, Andrey I.;Gladkikh, Polina D.;Glazachev, Yuri I.;Kirilyuk, Igor A. [Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 2036 - 2042]

57620-56-1 Synthesis

57620-56-1
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3317-61-1
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References

2H-Pyrrole-5-carboxylic acid, 3,4-dihydro-2,2-dimethyl-, 1-oxide

61856-91-5
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3317-61-1
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References

5,5-DIMETHYL-1-PYRROLINE N-OXIDE Related Search:

Pyrrole