Multi-step reaction with 8 steps
1.1: NaH / tetrahydrofuran / 0 °C
1.2: 98 percent / tetrahydrofuran / 5 h / Heating
2.1: NaH / 1,2-dimethoxy-ethane / 0 °C
2.2: 95 percent / 1,2-dimethoxy-ethane / 4 h / 25 °C
3.1: 87 percent / LiBH4 / tetrahydrofuran / 4 h / 25 °C
4.1: 94 percent / camphorsulfonic acid / CH2Cl2 / 0.17 h / 25 °C
5.1: O3 / CH2Cl2 / -78 °C
5.2: 97 percent / dimethyl sulfide / CH2Cl2 / 12 h / 20 °C
6.1: benzene / 2 h / Heating
7.1: LDA / diethyl ether; hexane / 1 h / -20 °C
7.2: diethyl ether; hexane / 12 h / -78 - 0 °C
7.3: 3.39 g / oxalic acid / hexane; H2O; diethyl ether / 0.5 h / 0 °C
8.1: KH / 1,2-dimethoxy-ethane; hexamethylphosphoric acid triamide / 0.5 h / 0 °C
8.2: dimethylformamide; hexamethylphosphoric acid triamide / 0.17 h / 0 °C
With
lithium borohydride; camphor-10-sulfonic acid; potassium hydride; sodium hydride; ozone; lithium diisopropyl amide;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; benzene;
DOI:10.1021/ja012010l