4-Hydroxymethylpyridine → HCID 59013880, compound

2-Chloro-3-pyridinol (500 mg, 3.86 mmol) was dissolved in 20 mL of tetrahydrofuran along with 4-pyridyl methanol (465 mg, 4.26 mmol) and triphenylphosphine (1.15 g, 4.38 mmol). To this solution was added diisopropylazodicarboxylate (840 μL, 4.27 mmol). The reaction was stirred at room temperature overnight under a nitrogen atmosphere. The solvent was removed under vacuum and the residue was dissolved in 50 mL of ethyl acetate. The reaction mixture was washed 4 times with 25 mL portions of water. Then, the product was extracted by washing 3 times with 25 mL portions of 0.5 M HCl. The acidic washes were neutralized with 1.0 M NaOH and the product was extracted back into ethyl acetate with 3 washes of 25 mL. The combined organic fractions were dried with magnesium sulfate and concentrated under vacuum to give 620 mg of 2-chloro-3-(pyridin-4-ylmethoxy)pyridine as a yellow solid.

1. customThe solvent was removed under vacuum
2. dissolutionthe residue was dissolved in 50 mL of ethyl acetate
3. washThe reaction mixture was washed 4 times with 25 mL portions of water
4. extractionThen, the product was extracted
5. washby washing 3 times with 25 mL portions of 0.5 M HCl
6. extractionthe product was extracted back into ethyl acetate with 3
7. dry with materialThe combined organic fractions were dried with magnesium sulfate
8. concentrationconcentrated under vacuum

ORD record

ord-0a48b9c5f90b444382d86edfdec39736

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08013156B2