Hydrochloric Acid → HCID 66618813, compound

HRID 406385Notes

Reaction equation

HRID 406385 reaction equation
C[Si](C)(C)[O:3][C:4]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([CH3:18])[CH:11]=1)([CH3:9])[C:5]([F:8])([F:7])[F:6].Cl.O.C(OCC)(=O)C>C1COCC1>[F:6][C:5]([F:7])([F:8])[C:4]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([CH3:18])[CH:11]=1)([OH:3])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 66618841HCID 66618841, compound

Product 1

HCID 66618813HCID 66618813, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trimethyl-[2,2,2-trifluoro-1-(4-methoxy-3-methylphenyl)-1-methylethoxy]silane (711 mg) was dissolved in THF (20 ml) and 1N HCl solution (20 ml) was added. After stirring at room temperature for 6 days, water and ethyl acetate were added to the reaction mixture and the organic layer was separated. The obtained organic layer was washed with brine and dried over anhydrous magnesium sulfate. After removing the drying agent, the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane→heptane:ethyl acetate 7:3) to obtain the title compound (442 mg). The property values of the obtained compound are as follows; 1H-NMR (CDCl3) δ (ppm): 1.76 (s, 3H), 2.24 (s, 3H), 3.84 (s, 3H), 6.83 (d, J=8.4 Hz, 1H), 7.34-7.37 (m, 2H).

Workup

  1. customthe organic layer was separated
  2. washThe obtained organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing the drying agent
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (elution solvent: heptane→heptane:ethyl acetate 7:3)

Sources & evidence

ORD record
ord-73270c06763b40b99ee7887ee462842b
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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