Hexane → 4-(3-Furyl)-7-methylcoumarin

Participants

Reaction Steps

To a solution of 3-bromofuran (1.9 g, 12.7 mmol) in dry Et2O (30 mL) at -70° C. was added BuLi in hexane (1.9M, 6.7 mL, 12.7 mmol) and the resulting mixture was stirred for 20 min. Trimethylborate (Aldrich) (1.4 mL, 12.7 mmol) was added dropwise and the mixture stirred for 20 min. A solution of the triflate from Step 4 in THF: H2O (24 mL, 6 mL) containing (Ph3P)4Pd (1.1 g, 0.97 mmol) was added and the reaction was heated to reflux for 16 h. The reaction mixture was cooled to r.t. and EtOAc was added and the organic phase washed with H2O (3×), brine, dried over MgSO4 and evaporated to give a white solid. A swish in EtOAc gave, after filtration, 1.8 g (82%) of the title compound.

Provenance & Evidence