Diethyl Ether → HCID 86680491, compound

To a solution of 5-(4-fluorophenyl)-1,3,4-thiadiazole-2-carbaldehyde (0.2 g, 0.96 mmol) in THF (8 mL) was added 3.0 M solution of ethyl magnesium bromide in diethyl ether (0.96 mL, 2.9 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred for 2 h. The reaction mixture was quenched with saturated ammonium chloride solution (15 mL) and water (15 mL), and extracted with ethyl acetate (100 mL). The organic extracts were dried over sodium sulphate and concentrated under reduced pressure to afford 1-(5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl)propan-1-ol as a yellow solid (0.10 g, 45% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.0-8.03 (m, 1H), 7.39-7.35 (m, 2H), 6.36 (d, 1H), 4.92-4.89 (m, 1H), 1.89-1.78 (m, 2H), 0.95 (t, 3H); LC-MS m/z calcd for [M+H]+ 239.06. found 239.1.

1. customThe reaction mixture was quenched with saturated ammonium chloride solution (15 mL) and water (15 mL)
2. extractionextracted with ethyl acetate (100 mL)
3. dry with materialThe organic extracts were dried over sodium sulphate
4. concentrationconcentrated under reduced pressure

ORD record

ord-aeb1b27a63754118966f32a2e7997b4d

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199975B2