2-Oxazolidinone,3-(1,2-propadienyl)-(9CI) synthesis
- Product Name:2-Oxazolidinone,3-(1,2-propadienyl)-(9CI)
- CAS Number:250728-91-7
- Molecular formula:C6H7NO2
- Molecular Weight:125.13
Yield:250728-91-7 65%
Reaction Conditions:
Stage #1: dimethylenecyclourethanewith potassium tert-butylate in dimethyl sulfoxide; for 1 h;Inert atmosphere;
Stage #2: propargyl bromide in dimethyl sulfoxide;toluene at 20; for 16 h;Inert atmosphere;
Steps:
Representative procedure
General procedure: To a solution of N-methyl p-toluenesulfonamide (17)(3.70 g, 20.00 mmol) in dry DMSO (40 mL) under an N2 or Ar atmosphere was added tBuOK (3.36 g, 30.00 mmol) and the resulting solution stirred for 1 h. To this solution was added propargyl bromide (2) (2.50 ml, 80% soln in toluene,22.00 mmol) dropwise over 40 min with care After the addition was complete, the mixture was stirred at room temperature overnight under N2 or Ar. The mixture was then diluted with H2O (100 mL) and the organic layer extracted with EtOAc (2 100 mL). The combined organic extracts were dried over Na2SO4, filtered and the solvent removed under vacuum. The crude reaction product was then purified by filtration through a pad of silica (EtOAc:/petroleum ether, 1:1) to yield a pale yellow solid which was recrystallised from CH2Cl2/petroleum ether giving the desired N-allenyl sulfonamide 18 as colourless plates (3.01 g, 68%)
References:
Bousfield, Thomas W.;Kimber, Marc C. [Tetrahedron Letters,2015,vol. 56,# 2,p. 350 - 352]
823-53-0
6 suppliers
inquiry
250728-91-7
7 suppliers
inquiry
