Sodium hydride → [4-(2-oxo-2H-pyran-4-yloxy)-naphthalen-1-yl]-carbamic acid tert-butyl ester

Participants

Reaction Steps

To a suspension of NaH (0.070 g of 60% oil dispersion) in 5 mL of anhydrous THF at 0° C. was added (4-hydroxy-naphthalen-1-yl)-carbamic acid tert-butyl ester (0.414 g) (Example 5). The mixture was stirred 20 min, then 4-chloro-2H-pyran-2-one (Helvitica Chemica. Acta, 1990, 73, 883) (0.208 g) was added and the reaction stirred 5 h at 0° C. Removal of the volatiles in vacuo provided a residue which was purified by flash chromatography on silica gel eluting with 33% EtOAc in hexanes. Concentration of the product rich fractions provided [4-(2-oxo-2H-pyran-4-yloxy)-naphthalen-1-yl]-carbamic acid tert-butyl ester.

Provenance & Evidence