Methyl iodide → Dimethyl methyl(trifluoromethyl)propanedioate

HRID 483262Notes

Reaction equation

HRID 483262 reaction equation
[F-].[Cs+].[CH3:3]OCCOCCOC.[CH3:12][O:13][C:14](=[O:24])[CH:15]([C:20]([F:23])([F:22])[F:21])[C:16]([O:18][CH3:19])=[O:17].CI>O>[CH3:3][C:15]([C:20]([F:22])([F:23])[F:21])([C:16]([O:18][CH3:19])=[O:17])[C:14]([O:13][CH3:12])=[O:24]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8150DiglymeHCID 25953Cesium fluorideHCID 201364Malonic acid, (trifluoromethyl)-, dimethyl ester

Product 1

HCID 12958001Dimethyl methyl(trifluoromethyl)propanedioateYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of dried CsF (9.11 g, 60 mmol), diglyme (41 ml), dimethyl(trifluoromethyl)malonate (4 g, 20 mmol), and methyl iodide (3.12 g, 22 mmol) was stirred overnight at room temperature. The reaction mixture was poured into water and the resultant oily layer and the ether-extract from the aqueous layer were combined and washed with water to remove diglyme. After drying over MgSO4, the ether was evaporated and the residue was subjected to distillation, giving dimethyl methyl(trifluoromethyl)malonate (2.56 g, 60%), b.p. 63°-65° C./10 mmHg. This product showed the following analytical properties: 19F NMR: δ--7.5 (s, CF3); 1H NMR: δ 3.81 (s, 6H, CO2CH3), 1.66 (s, CH3).

Workup

  1. extractionthe resultant oily layer and the ether-extract from the aqueous layer
  2. washwashed with water
  3. customto remove diglyme
  4. dry with materialAfter drying over MgSO4
  5. customthe ether was evaporated
  6. distillationthe residue was subjected to distillation

Sources & evidence

ORD record
ord-e91c00931ec648afa43406fb15af9090
Source dataset
uspto-grants-1986_03
Patent number
US04578503

Reaction notes

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