N,N,N',N'-Tetramethylethylenediamine → HCID 516434, compound

To a 1.6M solution of n-butyl lithium in hexane (1,38 mL, 2,2 mmol) was added tetramethylethylenediamine (0.3 mL, 2,2 mmol) under argon atmosphere at room temperature with stirring. Then 2-acetylfuran (242 mg, 2,2 mmol) in anhydrous THF was added dropwise to the mixture under ice cooling followed by stirring for 1 hour. To this mixture was added 1-ethyl-6-isopropylisatoic anhydride (250 mg, 1.1 mmol) in anhydrous THF. After stirring at room temperature overnight, the reaction mixture was diluted with saturated aqueous solution of ammonium chloride. The resulting organic layer was separated and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and then washed with saturated sodium chloride solution followed by drying with sodium sulfate. After removing ethyl acetate by evaporation in vacuo, the residue was subjected to preparative TLC(n-hexane:ethyl acetate=2:1) to separate the title compound followed by crystallization from diethyl ether. 1H-NMR(CDCl3) δ1.33(6H,d,CH(CH3)2), 1.55(3H,t,CH2CH3), 3.08(1H,septet,CH), 4.17(2H,q,NCH2), 6.48(1H,s,H-3), 6.56-6.58(1H,m,furan H-4′), 6.76(1H,dd,furan H-5′), 7.54(1H,d,H-8), 7.59(1H,dd,H-7), 7.63(1H,dd,furan H-3′), 8.34(1H,d,H-5)

1. stirringby stirring for 1 hour
2. stirringAfter stirring at room temperature overnight
3. customThe resulting organic layer was separated
4. concentrationconcentrated under reduced pressure
5. dissolutionThe residue was dissolved in ethyl acetate
6. washwashed with saturated sodium chloride solution
7. dry with materialby drying with sodium sulfate
8. customAfter removing ethyl acetate
9. customby evaporation in vacuo
10. customto separate the title compound
11. customfollowed by crystallization from diethyl ether

ORD record

ord-9024ead57b924b44874c35cfa84422f0

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06541470B1