Multi-step reaction with 12 steps
1.1: 1.58 g / boron trifluoride diethyl etherate / toluene / 1 h / 0 °C
2.1: Jones reagent / acetone / 0 - 23 °C
3.1: sodium borohydride / CH2Cl2; methanol / -90 - 23 °C
4.1: 10.5 g / 4-N,N-dimethylaminopyridine / CH2Cl2; pyridine / 4.5 h / 23 °C
5.1: 93 percent / NaCNBH3; acetic acid / 2.5 h
6.1: tributylphosphine; 2-nitrophenyl selenocyanate; pyridine / 40 h / 23 °C
6.2: 67 percent / aq. H2O2 / CH2Cl2 / 0 - 11 °C
7.1: mercury(II) acetate / tetrahydrofuran; H2O / 16 h / 23 °C
7.2: 88 percent / NaBH4 / tetrahydrofuran; H2O / 3 h
8.1: 28 percent / iodine; iodobenzene diacetate / hexane; CH2Cl2 / 2 h
9.1: 100 percent / potassium carbonate; methanol / tetrahydrofuran / 24 h / 40 °C
10.1: MgSO4 / benzene / 72 h / 23 °C
11.1: 90 percent / CH2Cl2; pyridine / 24 h / 45 °C
12.1: magnesium sulfate; NaCNBH3; acetic acid / toluene / 16 h / 23 °C
With
pyridine; methanol; sodium tetrahydroborate; ortho-nitrophenyl selenocyanate; jones reagent; tributylphosphine; [bis(acetoxy)iodo]benzene; mercury(II) diacetate; iodine; sodium cyanoborohydride; magnesium sulfate; potassium carbonate; acetic acid;
dmap; boron trifluoride diethyl etherate;
In
tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; acetone; toluene; benzene;
2.1: Jones oxidation / 6.1: Grieco reaction / 8.1: Suarez iodine(III) oxidation;
DOI:10.1021/ja0705487