Ethyl formate → sodium (Z)-3-ethoxy-3-oxoprop-1-en-1-olate
Reaction equation
[H-].[Na+:2].[C:3]([O:6][CH2:7][CH3:8])(=[O:5])[CH3:4].[CH:9](OCC)=[O:10]>C(OC(C)C)(C)C>[CH2:7]([O:6][C:3](=[O:5])/[CH:4]=[CH:9]\[O-:10])[CH3:8].[Na+:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
Sodium hydride (21.79 g, 545 mmol) was suspended in isopropyl ether (378 mL) in a 3-neck flask equipped with a thermometer adapter, addition funnel and a capped neck. Ethyl acetate (44.4 mL, 454 mmol) was added slowly via syringe through the capped neck. An internal temperature of 45° C. was maintained. Ethyl formate (78 mL, 962 mmol) was added via the addition funnel slowly, maintaining the temperature at 42° C. The reaction was allowed to stir overnight, at which point solid had crashed out. This solid was filtered and washed with ethyl ether (2×100 mL) and hexanes (200 mL) and the solid was dried to give the title compound.
Workup
- customequipped with a thermometer adapter, addition funnel and a capped neck
- temperaturemaintaining the temperature at 42° C
- filtrationThis solid was filtered
- washwashed with ethyl ether (2×100 mL) and hexanes (200 mL)
- customthe solid was dried
Sources & evidence
- ORD record
- ord-9d2fe0acb8b84be0a8783e2bb2a24971
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367706B2
Reaction notes
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