Diethyl Ether → HCID 86680491, compound

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH:13]=[O:14])=[N:10][N:9]=2)=[CH:4][CH:3]=1.[CH2:15]([Mg]Br)[CH3:16].C(OCC)C>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([CH:13]([OH:14])[CH2:15][CH3:16])=[N:10][N:9]=2)=[CH:6][CH:7]=1

Participants

Procedure

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.