Water → 1-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]-2-methoxyethanone
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][CH2:24][C:25](OC)=[O:26].O>O1CCCC1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[S:7][C:8]([C:25](=[O:26])[CH2:24][O:23][CH3:22])=[CH:9][N:10]=1Participants
6
Conditions
- Temperature
- -70 °C
Procedure
To a solution of 2-(1,3-dioxolan-2-yl)-1,3-thiazole (2.20 g) in tetrahydrofuran (50 mL) was slowly added a 1.6M n-butyllithium hexane solution (9.6 mL) at −70° C. under a nitrogen atmosphere. The reaction mixture was stirred at −70° C. for 1 hr, and methyl methoxyacetate (2.91 g) was added. The reaction mixture was warmed to room temperature, water 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 (2.00 g, yield 62%) was obtained as yellow crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). melting point 65-66° C.
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-2b153fa2f1cc42a69826329dc522f251
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318746B2
Reaction notes
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