Borane;tetrahydrofuran → HCID 90418623, compound

Temperature

0 °C

Into a 25-mL round-bottom flask (1 atm) purged and maintained with an inert atmosphere of nitrogen, was placed 3-methoxy-5-(4-methoxyphenyl)-1,2-thiazole-4-carboxylic acid (160 mg, 0.60 mmol, 1.00 equiv), tetrahydrofuran (4.0 mL). This was followed by the addition of BH3.THF(1 M) (1.83 mL) dropwise with stirring at 0° C. The resulting solution was stirred overnight at 45° C. in an oil bath. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:2). The reaction was then quenched by the addition of 5.0 mL of water. The resulting solution was extracted with 3×10.0 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 1×20 mL of sodium chloride. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a TLC-Plate with ethyl acetate/petroleum ether (1:2). This resulted in 63 mg (42%) of [3-methoxy-5-(4-methoxyphenyl)-1,2-thiazol-4-yl]methanol as a white solid. Mass spectrum (ESI, m/z): Calcd. for C12H13NO3S, 252.1 (M+H). found 252.1.

1. customInto a 25-mL round-bottom flask (1 atm) purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. stirringThe resulting solution was stirred overnight at 45° C. in an oil bath
4. customThe reaction was then quenched by the addition of 5.0 mL of water
5. extractionThe resulting solution was extracted with 3×10.0 mL of ethyl acetate
6. washThe resulting mixture was washed with 1×20 mL of sodium chloride
7. dry with materialThe mixture was dried over anhydrous sodium sulfate
8. concentrationconcentrated under vacuum
9. customThis resulted in 63 mg (42%) of [3-methoxy-5-(4-methoxyphenyl)-1,2-thiazol-4-yl]methanol as a white solid

ORD record

ord-3544c582e0f947018ea4e84d8e9f3e62

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1