4-trimethylsilylaniline → HCID 17912568, compound

HRID 963547Notes

Reaction equation

HRID 963547 reaction equation
[F:1][C:2]([F:10])=[CH:3][CH2:4][CH2:5][CH2:6][C:7](Cl)=[O:8].[CH3:11][Si:12]([CH3:21])([CH3:20])[C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1>O1CCCC1>[CH3:11][Si:12]([CH3:21])([CH3:20])[C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH:3]=[C:2]([F:10])[F:1])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 100349574-trimethylsilylanilineHCID 197938396,6-Difluorohex-5-enoic acid chloride

Product 1

HCID 17912568HCID 17912568, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

With cooling at 10°, 1.0 g of 6,6-difluorohex-5-enoic acid chloride is added to 1.0 g of 4-trimethylsilylaniline, 0.73 g of trithylamine and 10 mg of 4-N-pyrrolidinopyridine in 25 ml of tetrahydrofuran. The mixture is stirred for 2 hours at room temperature and then concentrated by evaporation in vacuo. The residue is taken up in toluene, the toluene phase is washed with water, dried over sodium sulfate and concentrated to dryness by evaporation. The residue is taken up in hexane:ethyl acetate (9:1) and filtered over silica gel. Evaporation of the filtrate yields the title compound having a melting point of 50°-51° (compound no. 1-1).

Workup

  1. temperatureWith cooling at 10°
  2. concentrationconcentrated by evaporation in vacuo
  3. washthe toluene phase is washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness by evaporation
  6. filtrationfiltered over silica gel
  7. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-3761c0dc94484fe6a08de3592d205b23
Source dataset
uspto-grants-1998_06
Patent number
US05763481

Reaction notes

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