Sulfuric Acid → ethyl 2-(3-chlorophenyl)-2-oxoacetate
Reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.C1COCC1.[Cl:16][C:17]1[CH:18]=[C:19]([Mg]Br)[CH:20]=[CH:21][CH:22]=1.S(=O)(=O)(O)O>C(OCC)C>[CH2:9]([O:8][C:1](=[O:7])[C:2]([C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:16])[CH:22]=1)=[O:4])[CH3:10]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Diethyl oxalate (4.4 g, 30.2 mmol) was dissolved in dry ethyl ether (30 mL) and freshly distilled THF (30 mL) and cooled to −78° C. with stirring, under a nitrogen atmosphere. Then added 3-chlorophenylmagnesium bromide (0.5 M in THF, 72.5 mL, 36.2 mmol) dropwise, via an addition funnel, while keeping the temperature between −75 to −78° C. The addition took approximately 90 minutes. After 3 hours, the reaction was quenched by the dropwise addition of 2N sulfuric acid (50 mL, 91 mmol) at −78° C. and upon completion of the addition, the mixture was allowed to return to room temperature. The mixture was extracted with ethyl ether (3×) and the combined ether extracts were washed with brine (2×), dried over magnesium sulfate, filtered, evaporated in vacuo and vacuum-dried to yield ethyl-(3-chlorophenyl)(oxo)acetate (6.5 g, HPLC RT=3.46 min, Method A; LCMS m/z=213).
Workup
- custombetween −75 to −78° C
- additionThe addition
- waitAfter 3 hours
- customto return to room temperature
- extractionThe mixture was extracted with ethyl ether (3×)
- washthe combined ether extracts were washed with brine (2×)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated in vacuo
- customvacuum-dried
Sources & evidence
- ORD record
- ord-aaf32d1302a34c4a84f09df8c0a7c47f
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07144899B2
Reaction notes
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