Iodoethane → HCID 58863679, compound

Temperature

0 °C

To a solution of diisopropylamine (0.42 g, 4.15 mmol) in tetrahydrofuran (7 ml) was added n-butyl lithium in hexane (1.56M, 2.2 ml, 3.43 mmol) under ice cooling, and the mixture was stirred for 15 minutes at 0° C. Thereto was added dimethyl (3-iodobenzyl)malonate (0.98 g, 2.82 mmol) in tetrahydrofuran (8 ml) under ice cooling, and the mixture was stirred for 10 minutes at 0° C. Thereto was added ethyl iodide (0.70 g, 4.49 mmol) and the mixture was stirred for 1 hour at 60° C. Additional ethyl iodide (0.60 g, 3.85 mmol) was added thereto and the mixture was stirred for 3 hours at 60° C. The reaction was quenched by an aqueous 5% potassium hydrogensulfate solution and extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution, and dried over magnesium sulfate. The solvent was removed and the residue was purified with silica gel chromatography (hexane:ethyl acetate=4:1→3:1) to give the subject compound (0.78 g, 73%).

1. stirringthe mixture was stirred for 10 minutes at 0° C
2. stirringthe mixture was stirred for 1 hour at 60° C
3. stirringthe mixture was stirred for 3 hours at 60° C
4. customThe reaction was quenched by an aqueous 5% potassium hydrogensulfate solution
5. extractionextracted with ethyl acetate
6. washThe organic layer was washed with an aqueous saturated sodium chloride solution
7. dry with materialdried over magnesium sulfate
8. customThe solvent was removed
9. customthe residue was purified with silica gel chromatography (hexane:ethyl acetate=4:1→3:1)

ORD record

ord-c32745f1119d4c019825dda36f6f8b09

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07220773B2