2-Butyne-1,4-diol → (4-Hydroxy-but-2-ynyloxy)-acetonitrile

Sodium hydride (60% dispersion in oil, 7.5 g, 188 mmol) was added to a solution of 2-butyne-1,4-diol (16.1 g, 187 mmol) in THF (150 mL) at 0° C. under nitrogen. After 1 h at 0° C., bromoacetonitrile (8.33 mL, 120 mmol) was added slowly and the reaction was allowed to warm to rt. After 22 h at rt, the reaction was quenched with 1 N HCl (150 mL) and extracted with EtOAc (3×150 mL). The combined extracts were washed with brine (150 mL), dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (CH2Cl2→2% MeOH/CH2Cl2, gradient) afforded 4.35 g (29%) of (4-hydroxy-but-2-ynyloxy)-acetonitrile.

1. waitAfter 22 h at rt
2. customthe reaction was quenched with 1 N HCl (150 mL)
3. extractionextracted with EtOAc (3×150 mL)
4. washThe combined extracts were washed with brine (150 mL)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customPurification of the residue by flash column chromatography on silica gel (CH2Cl2→2% MeOH/CH2Cl2, gradient)

ORD record

ord-a0263dc918064c5f93fc19fbc61dc920

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07179820B2