Tetrahydrofuran → HCID 117966871, compound

HRID 522438Notes

Reaction equation

HRID 522438 reaction equation
O1CCCC1.[S:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([S:22][CH2:23][C:24]([F:27])([F:26])[F:25])[CH:16]=1)C#N.[F:28][C:29]([Si](C)(C)C)([F:31])[F:30].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>C(OCC)(=O)C.CCCCCC>[F:28][C:29]([F:31])([F:30])[S:6][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([S:22][CH2:23][C:24]([F:27])([F:25])[F:26])[CH:16]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 552549(Trifluoromethyl)trimethylsilaneHCID 11078149TBAF tetrahydrofuranHCID 117899715HCID 117899715, compound

Product 1

HCID 117966871HCID 117966871, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 100 ml of tetrahydrofuran were added 1.5 g (4.3 mmol) of 5-thiocyanatopentyl-{4-methyl-3-(2,2,2-trifluoroethylthio)phenyl}ether and 1.8 g (13 mmol) of trifluoromethyltrimethylsilane. Thereto was added, at 0° C., 5 ml (5.0 mmol) of a tetra-n-butylammonium fluoride-tetrahydrofuran (1 mol/liter) solution. A reaction was carried out for 1 hour. After confirmation of the completion of the reaction, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=10:1), to obtain 1.3 g (yield: 77%) of an intended product.

Workup

  1. additionThereto was added, at 0° C.
  2. customAfter confirmation of the completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-02d8547932fd44eba077274a11a93ac3
Source dataset
uspto-grants-2016_05
Patent number
US09332754B2

Reaction notes

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