diisobutylaluminium hydride in toluene 1.5 h; Heating;

1: 1.) N,N'-carbonyldiimidazole / 1.) THF, RT, 1 h, 2.) THF, RT, overnight 2: dihydrobis(methoxyethanato-O,O')aluminate sodium / tetrahydrofuran / 2 h / Ambient temperature 3: diisobutylaluminium hydride (DIBAH) / toluene / 1.5 h / Heating View Scheme

1: 1.) N,N'-carbonyldiimidazole / 1.) THF, RT, 1 h, 2.) THF, RT, overnight 2: dihydrobis(methoxyethanato-O,O')aluminate sodium / tetrahydrofuran / 2 h / Ambient temperature 3: diisobutylaluminium hydride (DIBAH) / toluene / 1.5 h / Heating View Scheme

1: dihydrobis(methoxyethanato-O,O')aluminate sodium / tetrahydrofuran / 2 h / Ambient temperature 2: diisobutylaluminium hydride (DIBAH) / toluene / 1.5 h / Heating View Scheme

1: 1.) MeMgBr, 2.) anisole / 1.) Et2O, RT, 2.) 100 deg C, 2 h 2: 66 percent / EDC, DIPEA / dimethylformamide / 2 h / Ambient temperature 3: 85 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 4: DIBAH / toluene / 1.5 h / Heating View Scheme