Hydrochloric Acid → HCID 12958003, compound

HRID 483263Notes

Reaction equation

HRID 483263 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:15])[CH:6]([C:11]([F:14])([F:13])[F:12])[C:7]([O:9][CH3:10])=[O:8].Cl>CN(C)C=O>[F:12][C:11]([C:6]([C:7]([O:9][CH3:10])=[O:8])([C:5]([O:4][CH3:3])=[O:15])[C:11]([F:13])([F:14])[F:12])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]([O:4][CH3:3])=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 201364Malonic acid, (trifluoromethyl)-, dimethyl ester

Product 1

HCID 12958003HCID 12958003, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Into a mixture of sodium hydride (0.36 g, 15 mmol) and N,N-dimethylformamide (5 ml), a solution of dimethyl(trifluoromethyl)malonate (2.00 g, 10 mmol) in N,N-dimethylformamide (5 ml) was added dropwise with cooling the vessel in an ice-bath. After being stirred for 2 h at room temperature, the reaction mixture was poured into dilute aqueous HCl, and worked up as usual. Distillation under vacuum gave tetramethyl 2,4,4,4-tetrafluoro-1-butene-1,1,3,3-tetra-carboxylate (1.27 g, 70%), b.p. 122°-124° C./0.3 mmHg. Found: C: 40.74; H: 3.53%. Calcd.for C8H12O8F4 : C: 40.01; H: 3.36%. 19F NMR: δ--15.1 (d. CF3), +10.7 (q, =CF--). 1H NMR: δ 3.77 (s, CH3), 3.87 (s, CH3), 3.90 (COCH3)). IR: 1665 (C=C), 1750 (C=O) cm-1

Workup

  1. temperaturewith cooling the vessel in an ice-bath
  2. distillationDistillation under vacuum

Sources & evidence

ORD record
ord-d76a34aa595a40eda4048dea908c56de
Source dataset
uspto-grants-1986_03
Patent number
US04578503

Reaction notes

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