Triphenylphosphine → HCID 22650026, compound

HRID 393301Notes

Reaction equation

HRID 393301 reaction equation
Br[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=[CH2:13])[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:37][Si:38]([C:41]#[CH:42])([CH3:40])[CH3:39]>C(NC(C)C)(C)C.CCCCCC.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:37][Si:38]([CH3:40])([CH3:39])[C:41]#[C:42][C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=[CH2:13])[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 10107850HCID 10107850, compound

Product 1

HCID 22650026HCID 22650026, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 165397Cupric acetate monohydrateCatalystHCID 7912DiisopropylamineSolventHCID 8058HexaneSolvent

Procedure

To a stirred mixture of 4 (5.66 g, 20 mmol), dichlorobis(triphenylphosphine) palladium(II) (0.7 g, 1 mmol), copper(II) acetate hydrate (0.18 g, 1 mmol) and triphenyl-phosphine (0.52 g, 2 mmol) in 40 mL of diisopropyl amine was added trimethylsilyl acetylene (2.16 g, 22 mmol) and heated to reflux. On refluxing for an hour the mixture turns dark and solidifies. The reaction mixture was diluted with 50 mL of hexane and filtered. The filtrate was concentrated under reduced pressure and the residue was chromatographed over silica gel with hexane/methylene chloride (9:1 by volume) as eluant to yield 2.88 g (50 percent) of trimethyl[2-(5-methylene-5H-dibenzo[a,d]cyclohepten-10-yl)ethynyl)silane, 5, as a yellow oil.

Workup

  1. temperatureheated to reflux
  2. temperatureOn refluxing for an hour the mixture
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was chromatographed over silica gel with hexane/methylene chloride (9:1 by volume) as eluant

Sources & evidence

ORD record
ord-1938dc19cfc54d7684f8650cbf298e53
Source dataset
uspto-grants-2004_10
Patent number
US06806327B2

Reaction notes

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