2-Butyne-1,4-diol → (4-Hydroxy-but-2-ynyloxy)-acetonitrile
Reaction equation
[H-].[Na+].[CH2:3]([OH:8])[C:4]#[C:5][CH2:6][OH:7].Br[CH2:10][C:11]#[N:12]>C1COCC1>[OH:7][CH2:6][C:5]#[C:4][CH2:3][O:8][CH2:10][C:11]#[N:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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.