Ethyl Acetate → 2-(2-{2-[2-(2-Fluoro-ethoxy)-ethoxy]-ethoxy}-ethoxy)-1,1-dimethoxy-ethane

HRID 217553Notes

Reaction equation

HRID 217553 reaction equation
[CH3:1][O:2][CH:3]([O:22][CH3:23])[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16]OS(C)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.[F-:41].C(OCC)(=O)C>C(#N)C>[F:41][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH:3]([O:22][CH3:23])[O:2][CH3:1]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 59236870Methanesulfonic acid 2-(2-{2-[2-(2,2-dimethoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethyl ester

Product 1

HCID 592368632-(2-{2-[2-(2-Fluoro-ethoxy)-ethoxy]-ethoxy}-ethoxy)-1,1-dimethoxy-ethaneYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the sulfonate (Compound 6) (75 mg, 0.21 mmol) and TBAF (1.1 M in THF, 573 μl, 0.63 mmol) in acetonitrile (8 ml) was heated at 90° C. for 30 minutes. TLC (ethyl acetate) monitoring showed the reaction was completed. After cooling to ambient and evaporation of the solvent the residue was flashed (Ethyl acetate) to afford the product (56 mg, 93%) as colourless oil.

Workup

  1. temperatureAfter cooling to ambient and
  2. customevaporation of the solvent the residue

Sources & evidence

ORD record
ord-2ddeb037ade64fdc9a47cb1ebdf2557e
Source dataset
uspto-grants-2012_06
Patent number
US08197793B2

Reaction notes

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