1: 1.) NaBH4, BF3-etherate, 2.) 3 N aq. NaOH, 3.) 30percent aq. H2O2 / 1.) THF, 20-25 deg C, 20-25 min, 3.) THF, 30-35 deg C, 2 h 2: 76 percent / phosphorus tribromide / 20 h / 55 - 60 °C 3: 66 percent / liquid ammonia / 6 h 4: 1.) lithium amide, hexamethylphosphorotriamide / 1.) 20 deg C, 1 h, 2.) 40-45 deg C, 10 h 5: sodium borohydride, ethylenediamine / nickel acetate / aq. ethanol 6: pyridinium chlorochromate / CH2Cl2 / 7 h View Scheme

1: 1.) Mg / 1.) ether, 2.) ether, reflux, 16 h 2: 1.) NaBH4, BF3-etherate, 2.) 3 N aq. NaOH, 3.) 30percent aq. H2O2 / 1.) THF, 20-25 deg C, 20-25 min, 3.) THF, 30-35 deg C, 2 h 3: 76 percent / phosphorus tribromide / 20 h / 55 - 60 °C 4: 66 percent / liquid ammonia / 6 h 5: 1.) lithium amide, hexamethylphosphorotriamide / 1.) 20 deg C, 1 h, 2.) 40-45 deg C, 10 h 6: sodium borohydride, ethylenediamine / nickel acetate / aq. ethanol 7: pyridinium chlorochromate / CH2Cl2 / 7 h View Scheme

1: 76 percent / phosphorus tribromide / 20 h / 55 - 60 °C 2: 66 percent / liquid ammonia / 6 h 3: 1.) lithium amide, hexamethylphosphorotriamide / 1.) 20 deg C, 1 h, 2.) 40-45 deg C, 10 h 4: sodium borohydride, ethylenediamine / nickel acetate / aq. ethanol 5: pyridinium chlorochromate / CH2Cl2 / 7 h View Scheme

1: 66 percent / liquid ammonia / 6 h 2: 1.) lithium amide, hexamethylphosphorotriamide / 1.) 20 deg C, 1 h, 2.) 40-45 deg C, 10 h 3: sodium borohydride, ethylenediamine / nickel acetate / aq. ethanol 4: pyridinium chlorochromate / CH2Cl2 / 7 h View Scheme

1: sodium borohydride, ethylenediamine / nickel acetate / aq. ethanol 2: pyridinium chlorochromate / CH2Cl2 / 7 h View Scheme

1: 1.) lithium amide, hexamethylphosphorotriamide / 1.) 20 deg C, 1 h, 2.) 40-45 deg C, 10 h 2: sodium borohydride, ethylenediamine / nickel acetate / aq. ethanol 3: pyridinium chlorochromate / CH2Cl2 / 7 h View Scheme

pyridinium chlorochromate in dichloromethane 7 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;