hydrogenchloride; water in methanol 18 h; Inert atmosphereReflux;

1: 1.) NaH; 2.) (COCl)2, DMSO / 1.) THF, 60 deg C; 2.) CH2Cl2, r.t. 2: 83 percent / tetrahydrofuran / 0 °C 3: 89 percent / (COCl)2, DMSO / CH2Cl2 / Ambient temperature 4: 90 percent / FeCl3 / CH2Cl2 / Ambient temperature 5: 92 percent / p-TsOH 6: (COCl)2, DMSO / CH2Cl2 / Ambient temperature 7: KN(SiMe3)2 / tetrahydrofuran / 0 °C 8: 1.) PhSSPh; 2.) BF3*Et2O / 1.) irrad.,r.t., hexane; 2.) CH2Cl2, r.t. 9: 1N NaOH / methanol 10: SOCl2 / benzene / Heating 11: 70 percent / LiN(SiMe3)2 / tetrahydrofuran / -100 °C 12: 97 percent / NaBH4 / methanol / 0 °C 13: NCS, AgNO3 14: 10percent MeOH, CF3COOH / 60 °C 15: 68 percent / 2N NaOH / methanol / Ambient temperature 16: H2 / 10percent Pd/C / methanol View Scheme

1: 83 percent / tetrahydrofuran / 0 °C 2: 89 percent / (COCl)2, DMSO / CH2Cl2 / Ambient temperature 3: 90 percent / FeCl3 / CH2Cl2 / Ambient temperature 4: 92 percent / p-TsOH 5: (COCl)2, DMSO / CH2Cl2 / Ambient temperature 6: KN(SiMe3)2 / tetrahydrofuran / 0 °C 7: 1.) PhSSPh; 2.) BF3*Et2O / 1.) irrad.,r.t., hexane; 2.) CH2Cl2, r.t. 8: 1N NaOH / methanol 9: SOCl2 / benzene / Heating 10: 70 percent / LiN(SiMe3)2 / tetrahydrofuran / -100 °C 11: 97 percent / NaBH4 / methanol / 0 °C 12: NCS, AgNO3 13: 10percent MeOH, CF3COOH / 60 °C 14: 68 percent / 2N NaOH / methanol / Ambient temperature 15: H2 / 10percent Pd/C / methanol View Scheme

1: 83 percent / tetrahydrofuran / 0 °C 2: 89 percent / (COCl)2, DMSO / CH2Cl2 / Ambient temperature 3: 90 percent / FeCl3 / CH2Cl2 / Ambient temperature 4: 92 percent / p-TsOH 5: (COCl)2, DMSO / CH2Cl2 / Ambient temperature 6: KN(SiMe3)2 / tetrahydrofuran / 0 °C 7: 1.) PhSSPh; 2.) BF3*Et2O / 1.) irrad.,r.t., hexane; 2.) CH2Cl2, r.t. 8: 1N NaOH / methanol 9: SOCl2 / benzene / Heating 10: 70 percent / LiN(SiMe3)2 / tetrahydrofuran / -100 °C 11: 97 percent / NaBH4 / methanol / 0 °C 12: NCS, AgNO3 13: 10percent MeOH, CF3COOH / 60 °C 14: 68 percent / 2N NaOH / methanol / Ambient temperature 15: H2 / 10percent Pd/C / methanol View Scheme

1: 92 percent / p-TsOH 2: (COCl)2, DMSO / CH2Cl2 / Ambient temperature 3: KN(SiMe3)2 / tetrahydrofuran / 0 °C 4: 1.) PhSSPh; 2.) BF3*Et2O / 1.) irrad.,r.t., hexane; 2.) CH2Cl2, r.t. 5: 1N NaOH / methanol 6: SOCl2 / benzene / Heating 7: 70 percent / LiN(SiMe3)2 / tetrahydrofuran / -100 °C 8: 97 percent / NaBH4 / methanol / 0 °C 9: NCS, AgNO3 10: 10percent MeOH, CF3COOH / 60 °C 11: 68 percent / 2N NaOH / methanol / Ambient temperature 12: H2 / 10percent Pd/C / methanol View Scheme

1: 70 percent / LiN(SiMe3)2 / tetrahydrofuran / -100 °C 2: 97 percent / NaBH4 / methanol / 0 °C 3: NCS, AgNO3 4: 10percent MeOH, CF3COOH / 60 °C 5: 68 percent / 2N NaOH / methanol / Ambient temperature 6: H2 / 10percent Pd/C / methanol View Scheme

1: SOCl2 / benzene / Heating 2: 70 percent / LiN(SiMe3)2 / tetrahydrofuran / -100 °C 3: 97 percent / NaBH4 / methanol / 0 °C 4: NCS, AgNO3 5: 10percent MeOH, CF3COOH / 60 °C 6: 68 percent / 2N NaOH / methanol / Ambient temperature 7: H2 / 10percent Pd/C / methanol View Scheme

1: 1N NaOH / methanol 2: SOCl2 / benzene / Heating 3: 70 percent / LiN(SiMe3)2 / tetrahydrofuran / -100 °C 4: 97 percent / NaBH4 / methanol / 0 °C 5: NCS, AgNO3 6: 10percent MeOH, CF3COOH / 60 °C 7: 68 percent / 2N NaOH / methanol / Ambient temperature 8: H2 / 10percent Pd/C / methanol View Scheme

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / methanol; dichloromethane / 2 h / 20 °C / Inert atmosphere 1.2: 2 h / 0 °C / Inert atmosphere 2.1: Grubb's 2nd generation catalyst / dichloromethane / 24 h / Inert atmosphere; Reflux 3.1: 5 Pd(II)/C(eggshell); hydrogen / ethanol / 1 h / 760.05 Torr 4.1: hydrogenchloride; water / methanol / 18 h / Inert atmosphere; Reflux View Scheme

1: tetrahydrofuran / 2 h / 0 °C 2: water; toluene-4-sulfonic acid / toluene / 18 h / Reflux 3: RuCl2(tricyclohexylphosphine)2(benzylidene) / dichloromethane / 24 h / Inert atmosphere; Reflux 4: sodium tetrahydroborate; cerium(III) chloride / methanol / 20 °C 5: palladium 10 on activated carbon; hydrogen / methanol / 18 h / 20 °C 6: hydrogenchloride; water / 18 h / Reflux 7: Dowex 50WX8 / methanol View Scheme