2-Butyne-1,4-diol → Methyl [(4-hydroxybut-2-yn-1-yl)oxy]acetate

Sodium hydride (60% dispersion in oil, 2.32 g, 58 mmol) was added to a solution of 2-butyne-1,4-diol (5.0 g, 58 mmol) in THF (60 mL) at 0° C. under nitrogen. After 1 h at 0° C., methyl bromomethylacetate (5.5 mL, 58 mmol) was added and the reaction was allowed to warm to rt. After 18 h at rt, the reaction was quenched with 1 N HCl (60 mL) and extracted with EtOAc (3×100 mL). The combined extracts were washed with brine (1×100 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (CH2Cl2→5% MeOH/CH2Cl2, gradient) afforded 3.2 g (35%) of (4-hydroxy-but-2-ynyloxy)-acetic acid methyl ester.

1. waitAfter 18 h at rt
2. customthe reaction was quenched with 1 N HCl (60 mL)
3. extractionextracted with EtOAc (3×100 mL)
4. washThe combined extracts were washed with brine (1×100 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customPurification of the residue by flash column chromatography on silica gel (CH2Cl2→5% MeOH/CH2Cl2, gradient)

ORD record

ord-ef0148b150e840c5a4174154adc19643

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07179820B2