Multi-step reaction with 12 steps
1: 98 percent / BF3*OEt2
2: 79 percent / LiBH4 / methanol; tetrahydrofuran / 4 h / 0 °C
3: 88 percent / pTsOH / CH2Cl2 / 24 h / 20 °C
4: 27.4 g / Et3N / CH2Cl2 / 0.5 h / -20 °C
5: tetrahydrofuran / 1 h / 0 - 20 °C
6: 31.4 g / magnesium monoperoxy phthalate / ethanol / 0 °C
7: 24.1 g / CeCl3*7H2O; (COOH)2 / acetonitrile / 20 °C
8: 38.6 g / imidazole / dimethylformamide / 2 h / 20 °C
9: 85 percent / nBuLi / tetrahydrofuran; hexane / 2.33 h / -78 - 20 °C
10: 95 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 4 h / 20 °C
11: 97 percent / K2CO3 / dimethylformamide / 8 h / 20 °C
12: 72 percent / Jones' reagent / acetone / 6 h / 0 °C
With
1H-imidazole; lithium borohydride; n-butyllithium; jones' reagent; cerium(III) chloride; boron trifluoride diethyl etherate; oxalic acid; potassium carbonate; toluene-4-sulfonic acid; magnesium monoperoxyphthalate hexahydrate; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1002/ejoc.200400709