Dipotassium 2,3-dihydroxybutanedioate → [1-(4-ethylphenyl)-1H-imidazol-5-yl]methanol
Reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14](OCC)=[O:15])=[CH:12][N:11]=[CH:10]2)=[CH:5][CH:4]=1)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[K+]>O1CCCC1>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]([CH2:14][OH:15])=[CH:12][N:11]=[CH:10]2)=[CH:7][CH:8]=1)[CH3:2]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a −78° C. solution of ethyl 1-(4-ethylphenyl)-1H-imidazole-5-carboxylate (C17) (6.5 g, 27 mmol) in tetrahydrofuran (45 mL) was added lithium aluminum hydride (1 M solution in tetrahydrofuran, 27 mL, 27 mmol), and the reaction mixture was stirred at −78° C. for 0.5 hours, then warmed to room temperature and stirred for an additional 2 hours. Saturated aqueous potassium tartrate solution was added to quench the reaction. The aqueous layer was extracted with ethyl acetate (10 mL), and the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Purification of the resulting pale yellow oil using silica gel chromatography (Gradient: 0% to 5% methanol in ethyl acetate) provided the product. Yield: 3.8 g, 18.8 mmol, 70%. LCMS m/z 203.0 (M+1). 1H NMR (500 MHz, CDCl3) δ 1.29 (t, J=7.6 Hz, 3H), 2.73 (q, J=7.6 Hz, 2H), 4.57 (s, 2H), 2.35-2.53 (br s, 1H), 7.13-7.14 (br s, 1H), 7.35 (br AB quartet, JAB=8.5 Hz, ΔνAB=27 Hz, 4H), 7.62 (br s, 1H).
Workup
- temperaturewarmed to room temperature
- stirringstirred for an additional 2 hours
- customto quench
- customthe reaction
- extractionThe aqueous layer was extracted with ethyl acetate (10 mL)
- dry with materialthe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customPurification of the resulting pale yellow oil
- customprovided the product
Sources & evidence
- ORD record
- ord-55f1957566344598a16fff57c1f6f18e
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829010B2
Reaction notes
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