Trimethylsilylacetylene → 1-(4-Trimethylsilylethynyl-phenyl)-2,2-dimethylpropan-1-one

HRID 64646Notes

Reaction equation

HRID 64646 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].Br[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:10][CH:9]=1>C(NCC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:1][Si:2]([C:5]#[C:6][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:19])[C:15]([CH3:17])([CH3:16])[CH3:18])=[CH:10][CH:9]=1)([CH3:4])[CH3:3]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 128120801-(4-Bromophenyl)-2,2-dimethylpropan-1-one

Product 1

HCID 202368631-(4-Trimethylsilylethynyl-phenyl)-2,2-dimethylpropan-1-one

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

1.4 g Bis-(triphenylphosphine)-palladium dichloride and 0.19 g CuI are added, at room temperature, to a solution of 10.5 g trimethylsilylacetylene and 23.6 g 1-(4-bromophenyl)-2,2-dimethylpropan-1-one in 350 ml absolute diethylamine. The reaction mixture is stirred during 20 hours at room temperature, evaporated to dryness at the rotary evaporator and the residue extracted several times with toluene. The toluene is evaporated off and the remaining tacky oil chromatographed on a silica-gel column with hexane/toluene 2:1 as mobile phase to give 1-(4-trimethylsilylethynyl-phenyl)-2,2-dimethylpropan-1-one.

Workup

  1. customevaporated to dryness at the rotary evaporator
  2. extractionthe residue extracted several times with toluene
  3. customThe toluene is evaporated off
  4. customthe remaining tacky oil chromatographed on a silica-gel column with hexane/toluene 2:1 as mobile phase

Sources & evidence

ORD record
ord-d777a7d27d1e436e82168eafc3bd86d5
Source dataset
uspto-grants-1986_09
Patent number
US04609668

Reaction notes

Loading…