N,N,N',N'-Tetramethylethylenediamine → HCID 53833864, compound

To 300 mL of THF was added with cooling (ice-bath) 300 mL (0.3 mol) of 1M TiCl4 in methylene chloride and the mixture was stirred for 10 min. To the above mixture was added at room temperature 90.5 mL (0.6 mol) of TMEDA, the mixture was stirred for 10 min, and then 44.12 g (0.675 mol) of Zn dust was added with cooling to maintain the mixture at room temperature and stirred for 40 min. To the resulting reaction mixture was added dropwise to a mixture of ethyl 3-furoate (10.5 g, 0.075 mol), 31 g (0.165 mol) of dibromoethane in 200 mL of THF, and the mixture was stirred at room temperature for 2.5 h. After adding 90 mL of aqueous potassium carbonate solution, the mixture was concentrated in vacuo, the residue was diluted with 20 g of basic alumina, passed through a basic alumina column (ether/YEA 200:1), and the eluent was concentrated. The residue was triturated in ether (200 mL), filtered, and the filtrate was distilled (80-95° C./25 mm) to afford 6.2 g (54.3%) of 1-(3-furyl)-1-ethoxy-2- methylethylene (Formula l/I: R3 =CH3 ;R4 =H; R6 =CH3CH2O;R5 =3-Furyl; and Formula III: R3 =H;R4 =CH3 ;R6 =3-Furyl; R5 =CH3H2O).

1. stirringthe mixture was stirred for 10 min
2. temperaturewith cooling
3. stirringstirred for 40 min
4. customTo the resulting reaction mixture
5. stirringthe mixture was stirred at room temperature for 2.5 h
6. concentrationthe mixture was concentrated in vacuo
7. additionthe residue was diluted with 20 g of basic alumina
8. concentrationthe eluent was concentrated
9. customThe residue was triturated in ether (200 mL)
10. filtrationfiltered
11. distillationthe filtrate was distilled (80-95° C./25 mm)

ORD record

ord-890b521151d148d6ac87282c67673b5a

Source dataset

uspto-grants-1997_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05631264