Bis(trimethylsilyl)carbodiimide → HCID 58424747, compound

Participants

Reaction Steps

To a solution of 3-(4-oxo-2-((tetrahydrofuran-2-yl)methyl)chroman-6-yl)benzonitrile (233 mg, 0.70 mmol) in anhydrous DCM (18 mL) under N2 atmosphere was added 1 M TiCl4 (in DCM, 1.4 mL, 1.4 mmol) dropwise within 15 min at room temperature. It was stirred another 1 h after the addition. To this mixture was added Bis-trimethylsilylcarbodiimide (0.287 g, 0.35 mL, 1.54 mmol) dropwise. The resulting mixture was stirred overnight after the addition. The reaction mixture was poured into ice-water (25 g), and stirred for 30 min, then it was transferred to a separating funnel, the separated aqueous phase was extracted twice with DCM (2×30 mL). The combined organic phases were dried over anhydrous Na2SO4, and filtered, and concentrated to give N-(6-(3-cyanophenyl)-2-((tetrahydrofuran-2-yl)methyl)chroman-4-ylidene)cyanamide as light brown solid, which was used for next step without further purification. MS ESI +ve m/z 358 (M+H)+.

Provenance & Evidence