1: 50percent aq. NaOH, BuNEt3Cl / CH2Cl2 2: (i-Bu)2Al-O-C6H2-(2,6-di-t-Bu,4-Me) / CH2Cl2 / -78 °C 3: (i-Bu)2AlH View Scheme

1: K2CO3 / 5 h / 20 °C 2: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C 3: 85 percent / pyridine / 2 h / 5 °C 4: 0.24 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C 5: 2.) 1 N hydrochloric acid / 1.) benzene, 20 deg C, 3 h, 2.) 10 min 6: 90 percent / acetone / 1.5 h / -45 °C 7: CrO3/pyridine / CH2Cl2 8: aq. acetic acid / methanol / 0.08 h View Scheme