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0 °C

Into a 100-mL round-bottom flask, was placed 3-chloro-5-(2-methylphenyl)-1,2-thiazole-4-carboxylic acid (3 g, 11.82 mmol, 1.00 equiv), tetrahydrofuran (30 mL). This was followed by the addition of BH3(1M) (30 mL) dropwise with stirring at 0° C. The resulting solution was stirred overnight at 30° C. The reaction was then quenched by the addition of 30 mL of methanol. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (26/84). The collected fractions were combined and concentrated under vacuum. This resulted in 260 mg (9%) of [3-chloro-5-(2-methylphenyl)-1,2-thiazol-4-yl]methanol as yellow oil.

1. customInto a 100-mL round-bottom flask, was placed
2. additionThis was followed by the addition of BH3(1M) (30 mL) dropwise
3. stirringThe resulting solution was stirred overnight at 30° C
4. customThe reaction was then quenched by the addition of 30 mL of methanol
5. concentrationThe resulting mixture was concentrated under vacuum
6. concentrationconcentrated under vacuum
7. customThis resulted in 260 mg (9%) of [3-chloro-5-(2-methylphenyl)-1,2-thiazol-4-yl]methanol as yellow oil