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
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.
Workup
- customInto a 50-mL round-bottom flask, was placed
- customThe reaction was then quenched by the addition of 1.5 g of ice/salt
- filtrationThe solids were filtered out
- extractionThe resulting solution was extracted with 3×10 mL of ethyl acetate
- concentrationconcentrated under vacuum
- customThis resulted in 260 mg (42%) of [3-chloro-5-(2-methylphenyl)-1,2-thiazol-4-yl]methanol as yellow oil
Sources & evidence
- ORD record
- ord-b8b637ad627e464b8e690873d115c4d4
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067898B1
Reaction notes
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