Ethyl formate → 58986-28-0

HRID 1951282Notes

Reaction equation

HRID 1951282 reaction equation
[H-].[Na+:2].[C:3]([O:6][CH2:7][CH3:8])(=[O:5])[CH3:4].[CH:9](OCC)=[O:10]>O(C(C)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

HCID 8025Ethyl formateHCID 8857Ethyl AcetateHCID 24758Sodium hydride

Product 1

HCID 2367822458986-28-0

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

To a mixture of sodium hydride, 60% (1.07 g, 26.7 mmol) and iPr2O (40 mL) at RT was added ethyl acetate (2.36 ml, 24.1 mmol) in one portion. The internal temperature was adjusted to 40° C. After 5 minutes, ethyl formate (3.87 ml, 48.1 mmol) was added dropwise such that the internal temperature did not rise above 42° C. After the addition was complete, the solution was stirred at RT for 16 hr. The mixture was filtered under Argon and the solid rinsed with hexanes. The resulting white solid, sodium (Z)-3-ethoxy-3-oxoprop-1-en-1-olate, was advanced without further purification.

Workup

  1. customwas adjusted to 40° C
  2. customdid not rise above 42° C
  3. additionAfter the addition
  4. filtrationThe mixture was filtered under Argon
  5. washthe solid rinsed with hexanes
  6. customThe resulting white solid, sodium (Z)-3-ethoxy-3-oxoprop-1-en-1-olate, was advanced without further purification

Sources & evidence

ORD record
ord-5317b09913224fe79ad28d2b7290df8f
Source dataset
uspto-grants-2013_03
Patent number
US08404694B2

Reaction notes

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