Dimethylformamide → Ethyl trimethylsilyldifluoroacetate

HRID 2405146Notes

Reaction equation

HRID 2405146 reaction equation
[Mg].Cl[Si:3]([CH3:6])([CH3:5])[CH3:4].CN(C=O)C.Cl[C:13]([F:20])([F:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>O>[CH2:17]([O:16][C:14](=[O:15])[C:13]([F:20])([F:19])[Si:3]([CH3:6])([CH3:5])[CH3:4])[CH3:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 67843Acetic acid, 2-chloro-2,2-difluoro-, ethyl ester2×HCID 5462224Magnesium

Product 1

HCID 2758940Ethyl trimethylsilyldifluoroacetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

According to the above-described scheme, magnesium (243 mg, 10.0 mmol), chlorotrimethylsilane (Me3SiCl; 2.17 g, 20.0 mmol) and DMF (15 mL) were put into a two-neck reaction tube under nitrogen atmosphere. Ethyl chlorodifluoroacetate (Compound 3; 793 mg, 624 μL, 5.0 mmol) was added thereto with the reaction container being cooled in water bath, and then the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was extracted with diethyl ether and washed with water, and an organic layer was dried with anhydrous sodium sulfate. Diethyl ether was distilled away under reduced pressure, and by carrying out the production by silica gel column chromatography, difluorotrimethylsilanylacetic acid ethyl ester (Compound 3a) was obtained with a yield of 43%.

Workup

  1. customwere put into a two-neck reaction tube under nitrogen atmosphere
  2. extractionThe reaction mixture was extracted with diethyl ether
  3. washwashed with water
  4. dry with materialan organic layer was dried with anhydrous sodium sulfate
  5. distillationDiethyl ether was distilled away under reduced pressure

Sources & evidence

ORD record
ord-d06abf04b9144a0097d667297e56d493
Source dataset
uspto-grants-2014_08
Patent number
US08802886B2

Reaction notes

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