p-Fluoronitrobenzene → HCID 58994995, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of lithium diisopropylamide (12.2 mL, 22.0 mmol, 1.8 M) in 40 mL of THF at −78° C. was added tetrahydro-pyran-4-carboxylic acid methyl ester (2.88 g, 20.0 mmol) dropwise. The resulting mixture was stirred at −78° C. for 15 min, warmed to RT. 1,3-Dimethyl-tetrahydro-pyrimidin-2-one (2.69 g, 22.0 mmol) was added. The reaction was cooled to −78° C. again, 1-fluoro-4-nitro-benzene (3.10 g, 22.0 mmol) was added slowly. The resulting mixture was warmed to RT and stirred for 1 d under Ar. The reaction was treated with 30 mL of saturated NH4Cl and extracted with 80 mL of EtOAc. The organic extract was washed with H2O (50 mL), brine (20 mL), dried (Na2SO4) and concentrated. The residue was purified by flash chromatography on silica gel (5-20% EtOAc/hexane) to give 1.61 g (30%) of the title compound as a yellow solid. 1H-NMR (CDCl3; 400 MHz): δ 8.21 (d, 1H, J=9.0 Hz), 7.56 (d, 1H, J=9.0 Hz), 3.97 (m, 2H), 3.70 (s, 3H), 3.57 (m, 2H), 2.56 (m, 2H), 2.00 (m, 2H).

Provenance & Evidence