1: 69 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature 2: 1.) Zn, PPh3 / 1.) CH2Cl2, RT, 72 h, 2.) CH2Cl2, RT, 96 h 3: 1.) MeLi / 1.) THF, Et2O, a) -78 deg C, 1 h, b) RT, 3 h, 2.) THF, Et2O, RT, 17 h 4: 1.) CuI / 1.) THF, Et2O, from -10 deg C to 0 deg C, 2.) THF, Et2O, -78 deg C, 7.5 h 5: LiAlH4 / diethyl ether / 6 h / Ambient temperature View Scheme

1: (i) TsCl, Py, (ii) /BRN= 3587243/ 2: aq. NaOH 3: SOCl2 4: (i) SnCl4, (ii) DBN View Scheme

lithium aluminium tetrahydride in diethyl ether

lithium aluminium tetrahydride in diethyl ether 7 h; Heating;

1: 8 h / 150 °C 2: KOH / H2O / Heating 3: LiAlH4 / diethyl ether / Heating View Scheme

1: (i) TsCl, Py, (ii) /BRN= 3587243/ 2: aq. NaOH 3: SOCl2 4: (i) SnCl4, (ii) LiAlH4 View Scheme

1: (i) TsCl, Py, (ii) /BRN= 3587243/ 2: aq. NaOH View Scheme

Multistep reaction;

toluene-4-sulfonic acid in toluene T=110 - 120°C; 8 h;

potassium carbonate in acetone T=50°C; 8 h;