HCID 617437, compound → HCID 90418369, compound

Temperature

50 °C

Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 3-chloro-5-phenyl-1,2-thiazole-4-carboxylic acid (500 mg, 1.88 mmol, 1.00 equiv, 90%), chlorobenzene (2 mL), BH3 (3.1 mL, 3.00 equiv) at 0° C. The resulting solution was stirred for 12 h at 50° C. in an oil bath. The reaction was then quenched by the addition of 10 mL of sodium bicarbonate/H2O. The resulting solution was extracted with 3×10 mL of ethyl acetate and the organic layers combined. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:4). This resulted in 80 mg (18%) of (3-chloro-5-phenyl-1,2-thiazol-4-yl)methanol as a white solid.

1. customInto a 25-mL round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. customat 0° C
4. customThe reaction was then quenched by the addition of 10 mL of sodium bicarbonate/H2O
5. extractionThe resulting solution was extracted with 3×10 mL of ethyl acetate
6. customThis resulted in 80 mg (18%) of (3-chloro-5-phenyl-1,2-thiazol-4-yl)methanol as a white solid

ORD record

ord-d270127c3a554186b9ffa26e82b57fef

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1