Tert-Butyl nitrite → ethyl 5-(tetrahydro-2H-pyran-4-yl)thiophene-3-carboxylate

Participants

Reaction Steps

2-Amino-5-(tetrahydro-pyran-4-yl)-thiophene-3-carboxylic acid ethyl ester (1.79 g, 7 mmol) was added to a suspension of tert-butyl nitrite (10.5 mmol) and copper (II) chloride (7 mmol) in IMS (70 mL). The reaction was stirred for 15 minutes then saturated aqueous ammonium chloride (7 mL) was added and the mixture stirred for a further 15 minutes. The solvent was removed under vacuum and the residue partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulphate, filtered and the solvent evaporated to give the title compound (1.02 g). LCMS m/z 241 [M+H]+ RT=3.44 min (Analytical Method 4).

Provenance & Evidence