Ammonium Chloride → HCID 131721843, compound

Temperature

-78 °C

1-[2-(trimethylsilyl)ethoxy]methyl]-2-thiophenyl-imidazole (1.06 g, 3.46 mM) was dissolved in 40 ml of dry THF and the solution cooled to -78° C. under N2. Lithium diisopropylamide (3.46 ml, 5.19 mM, 1.5M solution in cyclohexane from Aldrich) was added via syringe, and the reaction solution stirred for 1 hour at -78° C. N-iodosuccinimide (0.85 g, 3.77 mM) in 10 ml of dry THF was added via syringe, and the reaction stirred for 30 minutes. The reaction mixture was added to 200 ml of saturated ammonium chloride, and extracted with 200 ml of ethyl acetate. The ethyl acetate layer was washed with saturated sodium bisulfite solution (150 ml), separated, dried over Na2SO4, filtered, and evaporated in vacuo to give a crude red brown oil. Purification by silica gel column chromatography using ethyl acetate/hexanes 1:9 gave 1.089 grams of 1-[2-(trimethylsilyl)ethoxy]methyl]-2-thiophenyl-5-iodo-imidazole (orange viscous oil).

1. stirringthe reaction stirred for 30 minutes
2. extractionextracted with 200 ml of ethyl acetate
3. washThe ethyl acetate layer was washed with saturated sodium bisulfite solution (150 ml)
4. customseparated
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. customevaporated in vacuo
8. customto give a crude red brown oil
9. customPurification by silica gel column chromatography

ORD record

ord-4b9b5b03c50345a0b4f50540b4eed10e

Source dataset

uspto-grants-2000_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06072057