Diethyl Ether → HCID 62651773, compound

Temperature

0 °C

To a solution of 2-(4-fluorophenyl)thiazole-5-carbaldehyde (500 mg, 2.41 mmol) in THF (25 mL) was added 3M methyl magnesium bromide in ether (1.61 mL, 4.83 mmol) slowly at 0° C. The reaction mixture stirred for 1 hour at 0° C. and then at room temperature for about 1 hour. The reaction mixture was quenched with saturated NH4Cl solution (25 mL), extracted with ethyl acetate (3×150 mL), the organic layer was dried over Na2SO4 and concentrated under reduced pressure to obtain crude product. The crude product was purified by flash chromatography (100-200μ; 30% ethyl acetate in hexane) to afford 1-(2-(4-fluorophenyl)thiazol-5-yl)ethanol as light yellow solid (420 mg, 78% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.93 (t, 2H), 7.67 (s, 1H), 7.30 (t, 2H), 5.71 (d, 1H), 5.01 (t, 1H), 1.45 (d, 3H); LC-MS m/z calculated for [M+H]+ 224.05, found 224.4

1. waitat room temperature for about 1 hour
2. customThe reaction mixture was quenched with saturated NH4Cl solution (25 mL)
3. extractionextracted with ethyl acetate (3×150 mL)
4. dry with materialthe organic layer was dried over Na2SO4
5. concentrationconcentrated under reduced pressure
6. customto obtain crude product
7. customThe crude product was purified by flash chromatography (100-200μ; 30% ethyl acetate in hexane)

ORD record

ord-e5978c7480fe4e278c667dd30b355fa5

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809372B2