Carbon Tetrachloride → Trimethylsilylmethyl 2-fluoro-2,2-dinitroethyl ether

HRID 1390528Notes

Reaction equation

HRID 1390528 reaction equation
C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S([O:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])(=O)=O.[F:20][C:21]([N+:27]([O-:29])=[O:28])([N+:24]([O-:26])=[O:25])[CH2:22]O.C(Cl)(Cl)(Cl)Cl>C(Cl)Cl>[F:20][C:21]([N+:27]([O-:29])=[O:28])([N+:24]([O-:26])=[O:25])[CH2:22][O:12][CH2:13][Si:14]([CH3:15])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 11430Potassium CarbonateHCID 28189Ethanol, 2-fluoro-2,2-dinitro-HCID 2760857(Trimethylsilyl)methyl Trifluoromethanesulfonate [Trimethylsilylmethylating Reagent]

Product 1

HCID 21731147Trimethylsilylmethyl 2-fluoro-2,2-dinitroethyl etherYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Potassium carbonate (6 g) was added to a solution of 3.5 g (0.0148 mol) of trimethylsilylmethyl trifluoromethanesulfonate and 2.3 g of 2-fluoro-2,2-dinitroethanol in 5 ml of methylene chloride, and the mixture was stirred for 16 hrs. This suspension was added with stirring to a mixture of 30 ml of ice water and 30 ml of carbon tetrachloride. The carbon tetrachloride layer was washed with 10 ml of water, dried over magnesium sulfate, and distilled to give 1.56 g (45%) of trimethylsilylmethyl 2-fluoro-2,2-dinitroethyl ether, bp 52° (0.75 mm).

Workup

  1. additionThis suspension was added
  2. washThe carbon tetrachloride layer was washed with 10 ml of water
  3. dry with materialdried over magnesium sulfate
  4. distillationdistilled

Sources & evidence

ORD record
ord-49eb490e0b2144e0a3dc99e2a1ca30ec
Source dataset
uspto-grants-1979_02
Patent number
US04139403

Reaction notes

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