1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C 2: 8.25 g / pyridine / 16 h / 20 °C View Scheme

acetic acid in ethyl acetate

1.1: 43 percent / AlCl3 / 1,2-dichloro-ethane / 3 h / 20 °C 2.1: triethylsilane; TFA / 1,2-dichloro-ethane / 3 h / 20 °C 3.1: 3.40 g / NaOMe; MeOH / 2 h / Heating 4.1: Et3N / CH2Cl2 / 1 h / 20 °C 5.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 6.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 6.2: 61 percent / ethanol / 3 h / 65 °C 7.1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C 8.1: 8.25 g / pyridine / 16 h / 20 °C View Scheme

1.1: 43 percent / AlCl3 / 1,2-dichloro-ethane / 3 h / 20 °C 2.1: triethylsilane; TFA / 1,2-dichloro-ethane / 3 h / 20 °C 3.1: 3.40 g / NaOMe; MeOH / 2 h / Heating 4.1: Et3N / CH2Cl2 / 1 h / 20 °C 5.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 6.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 6.2: 61 percent / ethanol / 3 h / 65 °C 7.1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C 8.1: 8.25 g / pyridine / 16 h / 20 °C View Scheme

1.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 1.2: 61 percent / ethanol / 3 h / 65 °C 2.1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C 3.1: 8.25 g / pyridine / 16 h / 20 °C View Scheme

1.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 1.2: 61 percent / ethanol / 3 h / 65 °C 2.1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C 3.1: 8.25 g / pyridine / 16 h / 20 °C View Scheme

1.1: Et3N / CH2Cl2 / 1 h / 20 °C 2.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 3.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 3.2: 61 percent / ethanol / 3 h / 65 °C 4.1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C 5.1: 8.25 g / pyridine / 16 h / 20 °C View Scheme

1.1: 3.40 g / NaOMe; MeOH / 2 h / Heating 2.1: Et3N / CH2Cl2 / 1 h / 20 °C 3.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 4.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 4.2: 61 percent / ethanol / 3 h / 65 °C 5.1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C 6.1: 8.25 g / pyridine / 16 h / 20 °C View Scheme

1.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 2.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 2.2: 61 percent / ethanol / 3 h / 65 °C 3.1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C 4.1: 8.25 g / pyridine / 16 h / 20 °C View Scheme

1.1: triethylsilane; TFA / 1,2-dichloro-ethane / 3 h / 20 °C 2.1: 3.40 g / NaOMe; MeOH / 2 h / Heating 3.1: Et3N / CH2Cl2 / 1 h / 20 °C 4.1: 16.0 g / NaI / butan-2-one / 2 h / Heating 5.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 5.2: 61 percent / ethanol / 3 h / 65 °C 6.1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C 7.1: 8.25 g / pyridine / 16 h / 20 °C View Scheme