2-(Trimethylsilyl)ethanol → HCID 59526323, compound

Temperature

0 °C

2-(Trimethylsilyl)ethanol (5.05 mL, 35.2 mmol) was taken up in THF (50 mL) and cooled to 0° C. Sodium hydride (1.48 g, 36.9 mmol) was added in 3 portions and the resulting mixture stirred at 0° C. for 15 minutes. This suspension was then added to a solution of 3,6-Dichloropyridazine (5 g, 33.6 mmol) in THF (50 mL) at 0° C. After stirring at 0° C. for 30 minutes, room temperature was attained and stirring continued overnight. Water was added followed by saturated NH4Cl and the reaction mixture was extracted into EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel column chromatography (2-20% EtOAc-hexanes) gave the title compound as a white solid.

1. stirringAfter stirring at 0° C. for 30 minutes, room temperature
2. stirringstirring continued overnight
3. extractionthe reaction mixture was extracted into EtOAc (2×)
4. washThe combined organic extracts were washed with brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customPurification of the residue by silica gel column chromatography (2-20% EtOAc-hexanes)

ORD record

ord-77b2ce7c0cad43b79b173eca16517e37

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367706B2