Methyl 5-nitro-2-furoate → HCID 58526527, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 5-nitrofuran-2-carboxylate (24) (171 mg, 1.0 mmol) in THF (2 mL) was added to a solution of TMPZnCl.LiCl (2) (1.3 M in THF, 0.85 mL, 1.1 mmol) at 25° C. and the reaction mixture was then stirred at this temperature for 30 min according to TP 2. After cooling down to −50° C., 3-bromocyclohexene (209 mg, 1.3 mmol) and CuCN.2LiCl (1.0 M solution in THF, 5 drops) were added and the resulting mixture was stirred for 1 h at this temperature. The reaction mixture was quenched with a sat. aq. NH4Cl solution (20 mL), extracted with diethyl ether (3×50 mL) and dried over anhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo. Purification by flash-chromatography (CH2Cl2/n-pentane, 1:2) furnished compound 26 (179 mg, 72%) as a yellowish oil.

Provenance & Evidence