Triethylamine → HCID 85422575, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(4-{1-[4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-one (5.63 g, 11.40 mmol) in THF (100 mL) is treated with 3.0 M CH3MgBr (5.7 mL, 17.24 mmol). The reaction is stirred for 1 h, quenched with satd NH4Cl (50 mL) at 0° C., diluted with EtOAc (100 mL), washed with 0.1 M HCl (2×50 mL), MgSO4 dried, and concentrated. The resulting residue is dissolved in THF (50 mL), and reacted with 1.0 M TBAF (12.6 mL, 12.6 mmol) for 1 h. The reaction is diluted with EtOAc (100 mL), washed with 0.1 M HCl (3×50 mL), brine (50 mL), MgSO4 dried, and concentrated. The resulting residue is dissolved in CH2Cl2 (100 mL), cooled to 0° C., treated with Et3N (1.7 mL, 12.38 mmol) and Tf2O (1.9 mL, 11.35 mmol). After stirring 5 m, the reaction is washed with 0.1 M HCl (2×50 mL), MgSO4 dried, concentrated, and chromatographed to give the title compound (5.30 g, 10.0 mmol, 87% for 3-steps). 1H NMR (CDCl3), δ 0.61 (t, J=7.1 Hz, 6H), 1.05(s, 9H), 1.34 (s, 3H), 2.05(q, J=7.1 Hz, 4H), 2.21 (s, 3H), 2.33 (s, 3H), 3.84 (d, J=8.9 Hz, 1H), 4.01 (d, J=8.9 Hz, 1H), 6.71 (d, J=8.3 Hz, 1H), 6.87 (d, J=2.2 Hz, 1H), 6.93 (dd, J=8.8, 2.6 Hz, 1H), 7.02-7.11 (m, 3H). LC/MS (m/z): calcd for C27H41NF3O5S (M+NH4)+: 548.7; found: 548.2.

Provenance & Evidence