Diisobutylaluminum hydride → 4-Thiazoleethanol, 2-(4-chlorophenyl)-

Participants

Reaction Conditions

Reaction Steps

Dissolve [2-(4-chloro-phenyl)-thiazol-4-yl]-acetic acid ethyl ester (107.4 g, 381.2 mmol) in THF (800 mL) and cool to 0-5° C. Slowly add DIBAL (1.0 M in THF, 800 mL, 800 mmol) over approximately 3.5 h keeping the temperature<5° C. After the addition is complete warm the resulting solution to room temperature and stir mechanically overnight. Cool the solution to 0-5° C. and slowly add additional DIBAL (150 mL) keeping the temperature<5° C. Stir at room temperature for 2.5 h, then cool to 0-5° C. and slowly quench over 5 h with aqueous saturated Rochelle's salt (2900 mL) keeping the temperature<10° C. Extract the mixture with EtOAc (2×3300 mL). Combine the organic solutions and concentrate in vacuo to give an oil (112.9 g). Dissolve the oil in toluene (600 mL) and concentrate in vacuo, then repeat. Dry the residue in vacuo for 6 h to give a residue weighing 107.4 g (110%). ES/MS m/z (35Cl) 240.1 [M+1]+.

Provenance & Evidence