18-Crown-6 → HCID 86628018, compound

Participants

Reaction Steps

To a solution of bis(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (3.18 g, 10.0 mmol) in THF (100 mL) at −78° C. was added 18-crown-6 (13.2 g, 50.0 mmol). The solution was stirred for 10 min then a solution of potassium hexamethyldisilazide in THF (0.91 M, 11.0 mL, 10.0 mmol) was added slowly. The reaction was stirred for 20 min then 3-bromo-5-chloro-2-hydroxy benzaldehyde (2.35 g, 10 mmol) was added. The reaction was allowed to stir at −78° C. for 2 hr, then was quenched with saturated NH4Cl (20 mL) The mixture was extracted with Et2O (3×100 mL) and the organic layer was dried (Na2SO4) and concentrated. Flash chromatography on silica gel (15% EtOAc/hexanes) gave, the title compound (2.48 g, 85%) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 7.88 (d, J=16.0 Hz, 1H), 7.50 (s, 1H), 7.44 (s, 1H), 6.57 (d, J=16.0 Hz, 1H), 3.84 (s, 3H); MS (ES) m/e 291, 293 (M+H)+.

Provenance & Evidence