Hydrochloric Acid → methyl (2-oxopropoxy)acetate
Reaction equation
C[Zn]C.[C:4]1(C)C=CC=CC=1.Cl[C:12]([CH2:14][O:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[O:13].Cl>[Cl-].[Na+].O.[CH2-]C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd+]>[CH3:20][O:19][C:17](=[O:18])[CH2:16][O:15][CH2:14][C:12](=[O:13])[CH3:4]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
2M Dimethyl zinc in toluene (21 mL, 42 mmol) and trans-benzyl(chloro)bis(triphenylphosphine)palladium(II) (0.57 g, 76 mmol) were treated with methyl 2-(chloroformylmethoxy)acetate (12.6 g, 76 mmol) dropwise over 0.5 hours at 0° C. under a nitrogen atmosphere. After stirring for 0.5 hours at 0° C., the mixture was allowed to warm to ambient temperature and stir for 16 hours. The reaction mixture was treated with 1 M HCl (40 mL) and brine (20 mL). The phases were separated and the organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel (1:2 ethyl acetate:hexanes) to provide the title compound (5.2 g).
Workup
- temperatureto warm to ambient temperature
- stirringstir for 16 hours
- customThe phases were separated
- dry with materialthe organic layer was dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by flash chromatography over silica gel (1:2 ethyl acetate:hexanes)
Sources & evidence
- ORD record
- ord-901c8b0859c549508be368bc160a31d2
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06538004B2
Reaction notes
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