Tetrahydrofuran toluene → HCID 178458170, compound

Participants

Reaction Steps

To a solution of Example 236B (1 g, 2.94 mmol) in THF (145 mL) was dropwise added 1.4 M MeMgBr in THF-toluene (8.4 mL, 11.76 mmol). The reaction mixture was slowly warmed to room temperature, stirred for 24 hours, quenched with aqueous NH4Cl, and extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated. The residue was purified by flash chromatography eluting with 50% ethyl acetate in hexane. The title compound (700 mg) was obtained at 70% yield. MS (DCI/NH3) m/z: 340.95 (M+H)+. 1H NMR (500 MHz, DMSO-D6) δ ppm 1.44 (s, 6H) 3.48 (s, 2H) 5.02 (s, 1H) 7.44 (dd, J=7.80, 1.25 Hz, 1H) 7.48 (m, 1H) 7.65 (s, 1H).

Provenance & Evidence