1.1: diisopropyl amine; n-butyllithium / diethyl ether; petroleum ether / 0.58 h / -78 °C 1.2: diethyl ether; petroleum ether / 1 h / -78 °C 2.1: 378 mg / triethylamine; methanesulfonyl chloride / CH2Cl2 / 4 h / 20 °C 3.1: lithium chloride / tetrahydrofuran / 2 h / 20 °C 3.2: n-butyllithium / tetrahydrofuran; petroleum ether / 0.08 h / -78 °C 3.3: 70 percent / tetrahydrofuran; petroleum ether / 0.5 h / -78 °C 4.1: 91 percent / PCC / CH2Cl2 / 48 h / 20 °C 5.1: cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C 6.1: 173 mg / mCPBA / CH2Cl2 / 1 h / 0 °C 7.1: 86 percent / Dess-Martin periodonane; sodium bicarbonate / CH2Cl2 / 1 h / 20 °C 8.1: magnesium bromide diethyl etherate / CH2Cl2 / 12 h / -78 °C 9.1: 1.0 g / pyridine; trifluoroacetic anhydride; triethylamine / CH2Cl2 / 3.5 h / 0 - 20 °C 10.1: magnesium bromide diethyl etherate; butanethiol / diethyl ether / 15 h / 20 °C 10.2: 77 percent / camphorsulfonic acid / CH2Cl2 / 18 h / 20 °C 11.1: 94 percent / cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C 12.1: triphenylphosphine; diethyl azodicarboxylate; 4-nitrobenzoic acid / tetrahydrofuran / 12 h / 20 °C 12.2: 86 percent / sodium methoxide / methanol / 1 h / 20 °C 13.1: 92 percent / imidazole / dimethylformamide / 2 h / 40 °C 14.1: t-butyllithium / diethyl ether; pentane / 0.5 h / -78 °C 14.2: 51 percent / TMEDA / diethyl ether; pentane / 0.08 h / -78 °C 15.1: 90 percent / Dess-Martin periodinane; sodium bicarbonate / CH2Cl2 / 1 h / 20 °C 16.1: TBAF / tetrahydrofuran / 0.5 h / 0 °C 17.1: 25 mg / HCl / 2-methyl-butan-2-ol / 2 h / 20 °C 18.1: 83 percent / imidazole / dimethylformamide / 2 h / 20 °C 19.1: 87 percent / DDQ / CH2Cl2; H2O / 0.5 h / 20 °C 20.1: 81 percent / pyridine / CH2Cl2 / 0.17 h / -78 °C 21.1: 9-BBN / tetrahydrofuran / 2 h / 40 °C 21.2: 37 percent / thallium carbonate; triphenylarsine / [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / tetrahydrofuran; dimethylformamide; H2O / 12 h / 20 °C 22.1: 78 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1.1: diisopropyl amine; n-butyllithium; triethylamine / chlorotrimethylsilane / tetrahydrofuran; petroleum ether / -78 - 0 &deg;C<br />1.2: bromine / tetrahydrofuran; petroleum ether / 2 h / -78 &deg;C<br />2.1: 5.0 g / lithium carbonate; lithium bromide / dimethylformamide / 4 h / 100 - 105 &deg;C<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3999191', constants.ctx, '0')">lithium carbonate</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '8128145', constants.ctx, '0')">lithium bromide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '605365', constants.ctx, '0')">N,N-dimethyl-formamide</a> <br />T=100 - 105&deg;C;&nbsp;4&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: 75 percent / KOH / Heating<br />2.1: diisopropyl amine; n-butyllithium; triethylamine / chlorotrimethylsilane / tetrahydrofuran; petroleum ether / -78 - 0 &deg;C<br />2.2: bromine / tetrahydrofuran; petroleum ether / 2 h / -78 &deg;C<br />3.1: 5.0 g / lithium carbonate; lithium bromide / dimethylformamide / 4 h / 100 - 105 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1.1: 70 percent / LDA; LiCl<br />2.1: 75 percent / KOH / Heating<br />3.1: diisopropyl amine; n-butyllithium; triethylamine / chlorotrimethylsilane / tetrahydrofuran; petroleum ether / -78 - 0 &deg;C<br />3.2: bromine / tetrahydrofuran; petroleum ether / 2 h / -78 &deg;C<br />4.1: 5.0 g / lithium carbonate; lithium bromide / dimethylformamide / 4 h / 100 - 105 &deg;C<br /> <br /> &nbsp;