1: NaOMe, N-chlorosuccinimide / tetrahydrofuran / 15 h / Ambient temperature 2: 85 percent / LiOH, H2O / methanol / 1 h / 0 °C View Scheme

N-chloro-succinimide; sodium methylate in tetrahydrofuran 15 h; Ambient temperature; Yield given;

<b>Multi-step reaction with 2 steps<br /> </b>1: 1.) sodium nitrite / 1) methanol, water, rt, 2 h; 2) pH 7, methanol, water, 0 deg C, 30 min<br />2: Me₂AlCl / CH₂Cl₂; hexane / 4 h / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 1.) sodium nitrite / 1) methanol, water, rt, 2 h; 2) pH 7, methanol, water, 0 deg C, 30 min<br />2: Me₂AlCl / CH₂Cl₂; hexane / 4 h / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 1.) KOt-Bu, 2,2,6,6-tetramethylpiperidine, n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) THF, hexane, -50 deg C, 20 min<br />2: Me₂AlCl / CH₂Cl₂; hexane / 4 h / -78 &deg;C<br /> <br /> &nbsp;