1-(Chloromethoxy)-2-methoxyethane → HCID 22147941, compound

To a solution of 3-iodo-5-nitro-1H-indazole (10.0 g, 34.6 mmol) in THF (50 ml) was added sodium bis(trimethylsilyl)amide (1M in THF, 48.4 mmol, 48.4 ml) and the solution stirred at room temperature for 20 minutes. 2-methoxyethoxymethyl chloride (4.9 g, 39.1 mmol, 4.5 ml) was added and the solution stirred at room temperature for 15 hours. The reaction was quenched with ammonium chloride (30 ml, saturated aqueous) and extracted into ethyl acetate (3×50 ml). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by flash column chromatography on silica gel (1:1 EtOAc:hexanes) to give the title compound as an orange solid (6.0 g). 1H NMR (400 MHz, CDCl3) δ 3.35 (3H, s), 3.50–3.52 (2H, m), 3.68–3.70 (2H, m), 5.86 (1H, s), 7.69 (1H, d), 8.38 (1H, d), 8.53 (1H, s). MS (ES+) m/e=378.

1. stirringthe solution stirred at room temperature for 15 hours
2. customThe reaction was quenched with ammonium chloride (30 ml, saturated aqueous)
3. extractionextracted into ethyl acetate (3×50 ml)
4. dry with materialThe combined organic extracts were dried (Na2SO4)
5. concentrationconcentrated in vacuo
6. customThe resulting residue was purified by flash column chromatography on silica gel (1:1 EtOAc:hexanes)

ORD record

ord-45e6f6e4960d4ace8d257b4bfe1b7418

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07041687B2