Citric Acid → 2-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]-1,1-dimethoxypropan-2-ol
Reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[S:7][CH:8]=[CH:9][N:10]=1.CCCCCC.C([Li])CCC.[CH3:22][O:23][CH:24]([O:28][CH3:29])[C:25](=[O:27])[CH3:26].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[S:7][C:8]([C:25]([OH:27])([CH3:26])[CH:24]([O:28][CH3:29])[O:23][CH3:22])=[CH:9][N:10]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
To a solution of 2-(1,3-dioxolan-2-yl)-1,3-thiazole (1.00 g) in tetrahydrofuran (20 mL) was slowly added a 1.6M n-butyllithium hexane solution (4.5 mL) at −70° C. under a nitrogen atmosphere. The reaction mixture was stirred at −70° C. for 30 min, and 1,1-dimethoxypropan-2-one (1.50 g) was added. The reaction mixture was warmed to room temperature, 10% aqueous citric acid solution was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (1.58 g, yield 90%) was obtained as a yellow oil from a fraction eluted with ethyl acetate-hexane (9:1, volume ratio). MS: 276 (MH+).
Workup
- temperatureThe reaction mixture was warmed to room temperature
- extractionthe mixture was extracted with ethyl acetate
- washThe ethyl acetate layer was washed with saturated brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-508054894adc44b097df154dab71a0ef
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318746B2
Reaction notes
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