Bis(trimethylsilyl)carbodiimide → HCID 178440660, compound

Participants

Reaction Steps

To a solution of 6-bromo-3′-tert-butylspiro[chroman-2,1′-cyclopentan]-4-one (200 mg, 0.60 mmol) in dried CH2Cl2 (10 mL) was added TiCl4 (1 M solution in DCM, 1.20 mmol) dropwise within 15 minutes. The mixture was stirred for 1 h after addition. To this mixture was added bis-trimethylsilylcarbodiimide (244 mg, 1.31 mmol) dropwise. The resulting mixture was stirred for 18 h after addition. The reaction mixture was poured into ice-water (30 g) and extracted with CH2Cl2. The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give (E)-N-(6-bromo-3′-tert-butylspiro[chroman-2,1′-cyclopentane]-4-ylidene)cyanamide (200 mg, crude), which was used for the next step without further purification.

Provenance & Evidence