Propargyl bromide → 4-[(2-Propynyloxy)methyl]benzyl alcohol

To a mixture of sodium hydride (400 mg, 8.4 mmol, 50% in oil) and tetrahydrofuran (30 mL) was added 1,4-benzenedimethanol (2.3 g, 17 mmol) at 0° C., and then N,N-dimethylformamide (30 mL) was added. The reaction mixture was stirred at room temperature for 10 minutes, after which propargyl bromide (1.0 g, 8.4 mmol) was added dropwise to the reaction mixture at 0° C. The reaction mixture was stirred at room temperature for 1 hour, after which water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed and saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue thus obtained was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:2) to obtain the title compound (860 mg, 58%).

1. stirringThe reaction mixture was stirred at room temperature for 1 hour
2. extractionwas extracted with ethyl acetate
3. washThe organic layer was washed
4. concentrationsaturated aqueous sodium chloride, and was concentrated under a reduced pressure
5. customThe residue thus obtained
6. customwas purified by NH silica gel column chromatography (heptane:ethyl acetate=3:2)

ORD record

ord-069a5b2d59254c22abe480ca278edf54

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07691882B2