lithium methanolate in tetrahydrofuran; methanol 4 h; Ambient temperature;

1: 1.) CH3SO2Cl, NEt3; 2.) NEt3 / 1.) THF, 0 deg C; 2.) 1.5 day, room temperature 2: 90 percent / 0.5M CH3OLi / tetrahydrofuran; methanol / 4 h / Ambient temperature View Scheme

1: 85 percent / aq. ethanol 2: 1.) MeMgI / 1.) Et2O-benzene 3: 1.) CH3SO2Cl, NEt3; 2.) NEt3 / 1.) THF, 0 deg C; 2.) 1.5 day, room temperature 4: 90 percent / 0.5M CH3OLi / tetrahydrofuran; methanol / 4 h / Ambient temperature View Scheme

1: 1.) MeMgI / 1.) Et2O-benzene 2: 1.) CH3SO2Cl, NEt3; 2.) NEt3 / 1.) THF, 0 deg C; 2.) 1.5 day, room temperature 3: 90 percent / 0.5M CH3OLi / tetrahydrofuran; methanol / 4 h / Ambient temperature View Scheme