Disodium 2,3-dihydroxybutanedioate → HCID 19741712, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 4-(bromomethyl)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzoate (1.59 g, 4.2 mmol) from Preparation 14 in THF 15 mL), cooled to -78° C. is treated with diisobutylaluminum hydride (1M, 10.4 mL, 10.4 mmol). The reaction mixture is stirred for 3.5 hours. The reaction mixture is treated with 20 mL of a saturated potassium-, sodium-tartrate solution, diethylether (200 mL) and is allowed to warm to room temperature. The organic phase is separated, dried (MgSO4), and concentrated. The residue is purified by silica gel chromatography (1% MeOH/CH2Cl2). An oil of 4-(bromomethyl)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzenemethanol is obtained (1.02 g, 74%).

Provenance & Evidence