Boron trifluoride etherate → HCID 89964136, compound

Participants

Reaction Steps

4-azido-4-(4-(trifluoromethyl)phenyl)chroman. To a solution of 4-(4-(trifluoromethyl)phenyl)chroman-4-ol (112 mg, 0.381 mmol) in toluene (4 mL), was added an ice bath and TMS azide (0.101 mL, 0.761 mmol). After 5 min., the solution was treated with BF3.OEt2 (0.048 mL, 0.381 mmol) dropwise. The solution turned from clear to light yellow during the addition. After 20 min, the reaction was quenched with MeOH (2 mL) and diluted with EtOAc (20 mL). The organic solution was washed with water (2×10 mL) and the organic layer concentrated in vacuo to give the title compound as a light yellow oil. MS (ESI pos. ion) m/z: 277.0 (M−N3). 1H NMR (CDCl3) δ: 7.57-7.65 (m, J=8.3 Hz, 2H), 7.41-7.52 (m, J=8.2 Hz, 2H), 7.26-7.33 (m, 1H), 6.81-7.03 (m, 3H), 4.30-4.44 (m, 1H), 4.21-4.30 (m, 1H), 2.23-2.34 (m, 1H), 2.12-2.23 (m, 1H).

Provenance & Evidence