2: p-toluenesulfonic acid, CH3OH / H2O; diethyl ether / 2 h / Heating View Scheme

methanol; lithium aluminium tetrahydride in tetrahydrofuran; diethyl ether 2 h; Ambient temperature; Yield given;

2: 1. BuLi, 2. paraformaldehyde / 1. pentane, ether, -10 deg C, 0.5 h, 2a. THF, 20 deg C, 45 min, 2b. reflux, 2.5 h 3: LiAlH4, CH3OH / diethyl ether; tetrahydrofuran / 2 h / Ambient temperature View Scheme

1: 1. BuLi, 2. paraformaldehyde / 1. pentane, ether, -10 deg C, 0.5 h, 2a. THF, 20 deg C, 45 min, 2b. reflux, 2.5 h 2: LiAlH4, CH3OH / diethyl ether; tetrahydrofuran / 2 h / Ambient temperature View Scheme