Tetrahydrofuran → [3-Chloro-5-(2-methylphenyl)-1,2-thiazol-4-yl]methanol
Reaction equation
[Cl:1][C:2]1[C:6]([C:7](OCC)=[O:8])=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[S:4][N:3]=1.O1CCCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[Cl:1][C:2]1[C:6]([CH2:7][OH:8])=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[S:4][N:3]=1Participants
4
Conditions
- Temperature
- 30 °C
Procedure
Into a 50-mL round-bottom flask, was placed ethyl 3-chloro-5-(2-methylphenyl)-1,2-thiazole-4-carboxylate (730 mg, 2.59 mmol, 1.00 equiv), tetrahydrofuran (10 mg, 0.14 mmol, 0.05 equiv). This was followed by the addition of LiAlH4 (296 mg, 7.80 mmol, 3.01 equiv), in portions at 0° C. The resulting solution was stirred for 2 h at 30° C. The reaction was then quenched by the addition of 1.5 g of ice/salt. The solids were filtered out. The resulting solution was extracted with 3×10 mL of ethyl acetate and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (25:75). This resulted in 260 mg (42%) of [3-chloro-5-(2-methylphenyl)-1,2-thiazol-4-yl]methanol as yellow oil. Mass spectrum (ESI, m/z): Calcd. for C11H10ClNOS, 240.0 (M+H). found 240.0.