Diisobutylaluminum hydride → (3-(5-Methylthiazol-2-yl)phenyl)methanol

Participants

Reaction Conditions

Reaction Steps

A cooled (−78° C.) solution of ethyl 3-(5-methylthiazol-2-yl)benzoate (388 mg; 1.57 mmol) in anh. toluene (4 ml) was treated with a solution of 1 M DIBAH in toluene (4.71 ml; 4.71 mmol), and the resulting mixture was further stirred at −78° C., under nitrogen, for 5 min., and then at 0° C. for 30 min. The obtained mixture was then treated successively with water (35 ml), 1 M aq. NaOH (11 ml), and aq. sat. NaHCO3 (30 ml). The separated aq. layer was further extracted with Et2O (2×100 ml). The mixed organic layers were then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=20/1) afforded (3-(5-methylthiazol-2-yl)phenyl)methanol as a pale yellow oil. LC-MS (conditions A): tR=0.58 min.; [M+H]+: 206.01 g/mol.

Provenance & Evidence