1,1,1,3,3,3-Hexafluoro-2-propanol → HCID 58042361, compound

Temperature

0 °C

A 60% dispersion of sodium hydride in mineral oil (450 mg, 11.25 mmol) was suspended in anhydrous tetrahydrofuran (10 mL). The suspension was cooled to 0° C. and 1,1,1,3,3,3-hexafluoropropan-2-ol (1.74 g, 10.35 mmol) was added over 15 minutes. The suspension was stirred 30 minutes and 2,3-dichloro-5-nitropyridine (1.50 g, 7.77 mmol) was added portionwise. The reaction was stirred at room temperature overnight then concentrated in vacuo. The crude residue was partitioned between ethyl acetate (50 mL) and water (50 mL). The aqueous layer was extracted by ethyl acetate (2×25 mL). Organic layers were combined, dried over magnesium sulfate, and concentrated in vacuo to afford the title compound as an orange oil (2.55 g, 100%).

1. stirringThe reaction was stirred at room temperature overnight
2. concentrationthen concentrated in vacuo
3. customThe crude residue was partitioned between ethyl acetate (50 mL) and water (50 mL)
4. extractionThe aqueous layer was extracted by ethyl acetate (2×25 mL)
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated in vacuo

ORD record

ord-4b33cfb377fc42ebb6a0b31d401a1b8c

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592629B2