toluene-4-sulfonic acid in methanol T=25°C;

N,N,N',N',N'',N''-hexamethylphosphoric triamide; n-butyllithium in tetrahydrofuran T=0°C; 1 h;

1: 2-(2-propynyloxy)-tetrahydro-2H-pyran With n-butyllithium in tetrahydrofuran; hexane T=-80 - 20°C; 0.75 h; 2: 1-iodo-n-heptane With tetra-(n-butyl)ammonium iodide in tetrahydrofuran; hexane T=20°C; 16 h; Heating / reflux;

1: p-TsOH 2: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide View Scheme

n-butyllithium in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide Alkylation;