Phenyl Bromoacetate → 2-Oxo-2-phenoxyethyl Lactate
Reaction equation
Br[CH2:2][C:3]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[C:12]([O-:17])(=[O:16])[CH:13]([CH3:15])[OH:14].C[N+](C)(C)C>CN(C)C=O>[C:12]([O:17][CH2:2][C:3](=[O:4])[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:16])[CH:13]([CH3:15])[OH:14]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Phenyl bromoacetate (45.0 g, 0.209 mol) was added to a stirring solution of tetramethylammonium lactate (40.7 g of an 88% aq soln, 1.05 eq) in 50 mL of dimethylformamide at room temperature. The resulting tetramethylammonium bromide which separated from the reaction mixture as a solid was removed by filtration and washed with ethyl acetate. The dimethylformamide and ethyl acetate solutions were combined and washed with a NaHCO3 /brine solution, the separated aqueous phase was extracted with CH2Cl2, and the organic phases were combined and dried with MgSO4. The solvent was removed and the resulting residue was chromatographed on silica gel (ethyl acetate/hexane) to give the title compound (14.7 g, 31%): 1H NMR δ1.50 (d, 3H, J=7.0), δ3.12 (d, 1H, J=5.3), δ4.40-4.49 (m, 1H), δ4.87 (d, 1H, J=16.1), δ4.99 (d, 1H, J=16.2), d 7.09-7.40 (5H, phenyl); HRMS calcd for C10H8O5TMS (M-CH3) 281.0845, obsd 281.0856.
Workup
- customThe resulting tetramethylammonium bromide which separated from the reaction mixture as a solid
- customwas removed by filtration
- washwashed with ethyl acetate
- washwashed with a NaHCO3 /brine solution
- extractionthe separated aqueous phase was extracted with CH2Cl2
- dry with materialdried with MgSO4
- customThe solvent was removed
- customthe resulting residue was chromatographed on silica gel (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-3b66eb9a16df45a1ae467392d45a747e
- Source dataset
- uspto-grants-1994_12
- Patent number
- US05371001
Reaction notes
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