Tetrahydrofuran → HCID 117899660, compound

HRID 522444Notes

Reaction equation

HRID 522444 reaction equation
O1CCCC1.[S:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[C:19]([S:21][CH2:22][C:23]([F:26])([F:25])[F:24])[C:18]([Cl:27])=[CH:17][C:16]=1[F:28])C#N.[F:29][C:30]([Si](C)(C)C)([F:32])[F:31].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(OCC)(=O)C.CCCCCC>[F:29][C:30]([F:32])([F:31])[S:6][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[C:19]([S:21][CH2:22][C:23]([F:26])([F:24])[F:25])[C:18]([Cl:27])=[CH:17][C:16]=1[F:28]

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 117899767HCID 117899767, compound

Product 1

HCID 117899660HCID 117899660, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 60 ml of tetrahydrofuran were added 3.9 g (10.1 mmol) of 5-thiocyanatopentyl-[4-chloro-2-fluoro-5-(2,2,2-trifluoroethylthio)phenyl]ether and 4.5 g (31.6 mmol) of trifluoromethyltrimethylsilane. Thereto was added 1.0 ml (1.04 mmol) of tetrahydrofuran solution (1 mol/liter) of tetra-n-butylammonium fluoride at 0° C., and reaction was carried out. The mixture was stirred overnight at room temperature. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=20:1), to obtain 2.60 g (yield: 60%) of an intended product.

Workup

  1. customreaction
  2. distillationThen, the solvent was distilled off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-c27455569daf4a4b8ac887b4d77942e4
Source dataset
uspto-grants-2016_05
Patent number
US09332754B2

Reaction notes

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