1.1: methanol; sodium methylate / 20 °C 1.2: Amberlite.(R). IR-120 H+ ion exchange 2.1: sodium hydride / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C / Inert atmosphere 2.2: 12 h / 20 °C / Inert atmosphere 3.1: N-bromosuccinmide; water / acetone / 3 h / 20 °C 4.1: acetic anhydride; dimethyl sulfoxide / 12 h / 30 °C View Scheme

in benzene 5 h; Ambient temperatureIrradiation;

1.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.25 h / 70 °C 1.2: 2 h / 20 °C 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C 2.2: -78 - 0 °C View Scheme

1: TfOH / H2O 2: DMSO / acetic anhydride View Scheme

1: sulfuric acid; acetic acid / water / 6 h / Reflux 2: acetic anhydride / dimethyl sulfoxide / 16 h / 20 °C / Inert atmosphere View Scheme

1: N-iodo-succinimide; water / acetone 2: acetic anhydride; dimethyl sulfoxide / 20 °C View Scheme

pyridine in dichloromethane 3.5 h; Title compound not separated from byproducts;

1: 95 percent / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - -70 °C 2: 94 percent / NaBH4 / tetrahydrofuran / 18 h / Ambient temperature 3: 1) trifluoroacetic anhydride, DMSO, 2) Et3N / 1) CH2Cl2, -75 to -65 deg C, 1 h, 2a) CH2Cl2, -75 to -65 deg C, 2b) to 0 deg C 4: 76 percent / 18-crown-6, K2CO3 / toluene / 8 h / Ambient temperature 5: 75 percent / NaBH4, cerous chloride / ethanol; tetrahydrofuran / 1 h / -78 - -70 °C 6: 52 percent / Ph3P, DEAD / tetrahydrofuran / a) -10 to -15 deg C, 1 h, b) ice-bath temp., 18 h 7: 74 percent / hydrazine monohydrate / methanol; tetrahydrofuran / 3 h / Ambient temperature 8: 62 percent / Na, NH3 liq. / tetrahydrofuran / 2 h / -70 - -65 °C View Scheme

1: diethyl ether 2: LiAlH4 / diethyl ether; tetrahydrofuran View Scheme

1: diethyl ether 2: H2 / Pd-C / methanol View Scheme