Diisobutylaluminum hydride → HCID 90417615, compound

Temperature

-78 °C

Into a 50-mL round-bottom flask (1 atm) purged and maintained with an inert atmosphere of nitrogen, was placed ethyl 3-(4-chlorophenyl)-5-(trifluoromethyl)-1,2-thiazole-4-carboxylate (1.0 g, 2.98 mmol, 1.00 equiv), toluene (5.0 mL). This was followed by the addition of DIBAL-H (20% in toluene) (4.23 g, 29.79 mmol, 2.00 equiv) dropwise with stirring at −78° C. The resulting solution was warmed to room temperature and stirred for 1 h at 30° C. The reaction progress was monitored by LCMS. The reaction was then quenched by the addition of 10 mL of water and 10 mL NH4Cl. The resulting solution was extracted with 3×20 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10). This resulted in 0.72 g (82%) of [3-(4-chlorophenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methanol as a yellow solid. Mass spectrum (ESI, m/z): Calcd. for C11H7ClF3NOS, 294.0 (M+H). found 294.0.

1. customInto a 50-mL round-bottom flask (1 atm) purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. temperatureThe resulting solution was warmed to room temperature
4. stirringstirred for 1 h at 30° C
5. customThe reaction was then quenched by the addition of 10 mL of water and 10 mL NH4Cl
6. extractionThe resulting solution was extracted with 3×20 mL of dichloromethane
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under vacuum
9. customThis resulted in 0.72 g (82%) of [3-(4-chlorophenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methanol as a yellow solid

ORD record

ord-6d62ce3b6e304d5dbeb8647807f1b677

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1