Water → HCID 66618821, compound

HRID 406356Notes

Reaction equation

HRID 406356 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]#[N:11].[OH-].[Na+].Br[CH2:17][CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].O>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Si:20]([O:19][CH2:18][CH2:17][CH:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:12])([F:13])[F:1])[C:10]#[N:11])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 764352-(Trifluoromethyl)phenylacetonitrileHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 66618821HCID 66618821, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

(2-Trifluoromethylphenyl)acetonitrile (3 g) and tetrabutylammonium bisulfate (550 mg) were suspended in toluene (30 mL), and a 50% sodium hydroxide aqueous solution (15 mL) was added dropwise under ice-cooling. After stirring for 10 minutes, (2-bromoethoxy)-tert-butyldimethylsilane (5.2 mL) was added at the same temperature. The mixture was brought back to room temperature and stirred overnight. Water was added to the reaction solution, followed by extraction with tert-butyl methyl ether. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (5 g). The property values of the compound are as follows.

Workup

  1. temperaturecooling
  2. customwas brought back to room temperature
  3. stirringstirred overnight
  4. extractionfollowed by extraction with tert-butyl methyl ether
  5. washThe resulting organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe drying agent was separated by filtration
  8. concentrationthe organic layer was concentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-14290ab3a76e4b4499edd07543d5ccbe
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

Loading…