N-ethyl-N,N-diisopropylamine in dichloromethane T=20°C; Etherification;

1: 83 percent / TEA / CH2Cl2 / 0 °C 2: 97 percent / Br2; AcOH / CH2Cl2 / 0.5 h / 20 °C 3: 96 percent / K2CO3 / acetone / 1 h / Heating 4: 97 percent / aq. NaOH / ethanol / 0.5 h / Heating 5: 97 percent / i-Pr2NEt / CH2Cl2 / 0 - 20 °C View Scheme

1: 97 percent / Br2; AcOH / CH2Cl2 / 0.5 h / 20 °C 2: 96 percent / K2CO3 / acetone / 1 h / Heating 3: 97 percent / aq. NaOH / ethanol / 0.5 h / Heating 4: 97 percent / i-Pr2NEt / CH2Cl2 / 0 - 20 °C View Scheme

1: 97 percent / aq. NaOH / ethanol / 0.5 h / Heating 2: 97 percent / i-Pr2NEt / CH2Cl2 / 0 - 20 °C View Scheme

1: 96 percent / K2CO3 / acetone / 1 h / Heating 2: 97 percent / aq. NaOH / ethanol / 0.5 h / Heating 3: 97 percent / i-Pr2NEt / CH2Cl2 / 0 - 20 °C View Scheme

1.1: 79 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 60 °C 2.1: CSA / methanol / 1 h / 20 °C 3.1: n-BuLi / diethyl ether; hexane / 0 - 20 °C 3.2: I2 / diethyl ether; hexane / 0 °C 4.1: 314 mg / conc. HCl / tetrahydrofuran / 0.25 h / 20 °C 5.1: 98 percent / K2CO3 / acetonitrile / 0.67 h / Heating 6.1: 93 percent / N,N,N',N'-tetramethylguanidine / CH2Cl2 / 24 h / 20 °C 7.1: H2; Rh[(COD)-(S,S)-Et-DuPHOS]+OTf- / ethyl acetate / 22 h / 50 °C / 25858.1 Torr 8.1: 100 percent / lithium hydroxide / methanol; tetrahydrofuran; H2O / 0 - 20 °C 9.1: 90 percent / methanol / 1 h / Heating 10.1: 89 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C 11.1: 93 percent / pyridine; DMAP / 30 h / 50 °C 12.1: TFA; anisole / CH2Cl2 / 9 h / 20 °C 13.1: 19.7 g / ethyl acetate / 1 h / Heating 14.1: 91 percent / TEA / CH2Cl2 / 1 h / 0 °C 15.1: 97 percent / DMAP / acetonitrile / 6.5 h / 20 °C 16.1: NaBH4; H2SO4 / ethanol; CH2Cl2 / 0 °C 17.1: 3.54 g / CSA; quinoline / toluene / 3 h / Heating 18.1: 83 percent / tris(dibenzylideneacetone)dipalladium(0); tris(o-tolyl)phosphine; TEA / acetonitrile / 2 h / Heating 19.1: aq. NaOH / methanol / 2.5 h / Heating 20.1: 106 mg / pyridine; DMAP / CH2Cl2 / 20 °C 21.1: TFA / CH2Cl2 / 4 h / 20 °C 22.1: 2.08 g / NaHCO3 / CH2Cl2; H2O / 0.17 h / 0 °C 23.1: dimethyldioxirane / methanol; acetone / 2 h / 0 °C 24.1: 652 mg / CSA / acetone / 0 - 20 °C 25.1: 94 percent / sodium cyanoborohydride; TFA / tetrahydrofuran / 0.5 h / 0 °C 26.1: 92 percent / imidazole / dimethylformamide / 2 h / 20 °C 27.1: 85 percent / guanidinium nitrate; NaOMe / methanol; CH2Cl2 / 2.5 h / 40 °C 28.1: 91 percent / K2CO3 / acetonitrile / 1 h / Heating 29.1: 82 percent / Red-Al / tetrahydrofuran; toluene / 0 °C 30.1: 73 percent / BF3*OEt2 / CH2Cl2 / 0 °C 31.1: 92 percent / pyridine; DMAP / 20 °C 32.1: 100 percent / aq. HF / acetonitrile / 3 h / 20 °C 33.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 0.67 h / 20 °C 34.1: 84 percent / H2 / Pd/C / tetrahydrofuran / 18 h / 20 °C / 760.05 Torr 35.1: 89 percent / i-Pr2NEt / CH2Cl2 / 3 h / Heating 36.1: 99 percent / K2CO3 / methanol / 0.5 h / 20 °C 37.1: 94 percent / WSCD*HCl; DMAP / CH2Cl2 / 0.17 h / 20 °C 38.1: 98 percent / hydrazine / acetonitrile / 1.33 h / 20 °C 39.1: TFA / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 40.1: 18.0 mg / pyridine; DMAP / 0.5 h / 20 °C 41.1: 92 percent / Zn; AcOH / diethyl ether / 2.5 h / 20 °C 42.1: 96 percent / AcOH; sodium cyanoborohydride / methanol / 1 h / 20 °C 43.1: 89 percent / Pd(PPh3)2Cl2; AcOH; n-Bu3SnH / CH2Cl2 / 0.33 h / 20 °C 44.1: 4-formyl-1-methylpyridinium benzenesulfonate / dimethylformamide; CH2Cl2 / 0.25 h / 20 °C 44.2: DBU / dimethylformamide; CH2Cl2 / 0.42 h / 20 °C 44.3: 54 percent / aq. citric acid / CH2Cl2; dimethylformamide / 0.67 h / 20 °C 45.1: 96 percent / sodium acetate / ethanol / 5.5 h / 20 °C 46.1: 93 percent / silver nitrate / acetonitrile; H2O / 17 h / 20 °C View Scheme