Diethyl Ether → HCID 18369547, compound

HRID 1699742Notes

Reaction equation

HRID 1699742 reaction equation
C([O:3][CH2:4][CH3:5])C.Cl[C:7](Cl)(Cl)[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=N.FC(F)(F)S(O)(=O)=O>C(OCC)(=O)C>[C:12]1([CH2:11][O:10][C:8]23[CH2:14][CH:13]([CH2:12][CH2:17][CH2:16]2)[CH2:5][C:4](=[O:3])[CH2:7]3)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 62406Trifluoromethanesulfonic acidHCID 144968Benzyl 2,2,2-trichloroacetimidate

Product 1

HCID 18369547HCID 18369547, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A diethyl ether solution of 260 mg of 2,2,2-trichloro-1-(phenylmethoxy)ethanimine synthesized in the production example 30 was added to 4 ml of a diethyl ether solution of the compound obtained in the production example 29 to prepare the homogeneous solution, and the flask was immersed in an ice water bath. The solution in the flask was mixed with 10 μl of trifluoromethanesulfonic acid, gradually heated up to room temperature, and simultaneously stirred for 17 hours. After the reaction was finished, the reaction solution was diluted with ethyl acetate and extracted. The obtained organic layers were integrated, sequentially washed with a saturated aqueous solution of sodium bicarbonate and with a saturated aqueous solution of sodium chloride, and then dried over Na2SO4. The solvent was distilled away under reduced pressure, and the residue was purified by column chromatography to obtain the title compound (120 mg, 70%).

Workup

  1. customobtained in the production example 29
  2. customto prepare the homogeneous solution
  3. customthe flask was immersed in an ice water bath
  4. extractionextracted
  5. washsequentially washed with a saturated aqueous solution of sodium bicarbonate and with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over Na2SO4
  7. distillationThe solvent was distilled away under reduced pressure
  8. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6ebdff1cdfdc4291a19d384ddf54a393
Source dataset
uspto-grants-2002_02
Patent number
US06348478B1

Reaction notes

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