Sodium hydride → Methyl 2-(2-thienylmethoxy)acetate

To a stirring 25 mL solution of 1.14 g (10 mmol) of thiophenemethanol in THF was added 0.24 g (10 mmol) of NaH. After the evolution of gas had ceased, 1.53 g (10 mmol) of methyl bromoacetate was added to the reaction. After 15 minutes, the reaction mixture was filtered. The solvent was removed under reduced pressure. The residue was then dissolved in 50 mL of EtOAc. The organic layer was washed with 3×50 mL of H2O, and was treated in the manner described above in Example 7. The residue was chromatographed to yield 0.91 g (49%) of product. Analysis calculated for C8H10O3S (M.W. 186.23): C, 51.60; H, 5.41. Found: C, 51.41; H, 5.60.

1. filtrationthe reaction mixture was filtered
2. customThe solvent was removed under reduced pressure
3. dissolutionThe residue was then dissolved in 50 mL of EtOAc
4. washThe organic layer was washed with 3×50 mL of H2O
5. additionwas treated in the manner
6. customThe residue was chromatographed

ORD record

ord-1aaf738cf8b94ac5b10bede53ce73ff0

Source dataset

uspto-grants-1996_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05576315