Dimethylformamide → HCID 12069553, compound

3-Pyridinol (1 eq.) was taken up in a 2:1 (v/v) mixture of DMF:THF (0.9 M). To this was then added, at −15° C., potassium tert-butoxide (1.1 eq.) and the resulting suspension was stirred at −15° C. for 25 min before chloromethyl methyl ether (1.1 eq.) was added dropwise over 15 min. The mixture was then warmed to RT over 1 h and allowed to stir at RT for another 2 h. The reaction mixture was then concentrated in vacuo and the resulting residue partitioned between EtOAc and water. The aqueous layer was separated and back-extracted with EtOAc. The combined organic extracts were then washed with water and brine, dried over Na2SO4, filtered through a short plug of SiO2 and the filtrate concentrated in vacuo to afford the title compound as a colorless oil.

1. additionTo this was then added, at −15° C.
2. additionwas added dropwise over 15 min
3. concentrationThe reaction mixture was then concentrated in vacuo
4. customthe resulting residue partitioned between EtOAc and water
5. customThe aqueous layer was separated
6. extractionback-extracted with EtOAc
7. washThe combined organic extracts were then washed with water and brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered through a short plug of SiO2
10. concentrationthe filtrate concentrated in vacuo

ORD record

ord-8da7c7bfe2d643559acc4f862a228028

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889714B2