Diethyl Ether → HCID 86680601, compound

To a solution of 2-(3-fluorophenyl)thiazole-5-carbaldehyde (0.320 g, 1.545 mmol) in THF (12 mL) was added 3.0 M solution of ethyl magnesium bromide in diethyl ether (1.28 mL, 3.86 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and stir for 3 h. The reaction mixture was quenched with saturated ammonium chloride solution (10 mL) and water (5 mL), extracted with ethyl acetate (50 mL), dried over sodium sulphate and concentrated under reduced pressure to obtain crude product. The crude compound was purified by Biotage Isolera® One chromatograph (using 15% ethyl acetate and hexane) to afford 1-(2-(3-fluorophenyl)thiazol-5-yl)propan-1-ol (0.18 g, 45% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.68 (d, 3H), 7.40 (q, 1H), 7.11 (t, 1H); 4.93 (t, 1H), 4.11 (q, 1H), 1.90-1.87 (m, 2H), 1.01 (t, 3H); LC-MS m/z calcd for [M+H]+ 238.06. found 238.0.

1. customThe reaction mixture was quenched with saturated ammonium chloride solution (10 mL) and water (5 mL)
2. extractionextracted with ethyl acetate (50 mL)
3. dry with materialdried over sodium sulphate
4. concentrationconcentrated under reduced pressure
5. customto obtain crude product
6. customThe crude compound was purified by Biotage Isolera® One chromatograph (using 15% ethyl acetate and hexane)

ORD record

ord-a30ab4b7fd464f83a83844dc6bb2d0eb

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199975B2