Trimethylsilylacetylene → HCID 67187907, compound

HRID 451610Notes

Reaction equation

HRID 451610 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH3:13])([CH3:12])[CH2:9][O:10][CH3:11])[CH:3]=1.[CH3:14][Si:15]([C:18]#[CH:19])([CH3:17])[CH3:16]>CC#N.CCN(CC)CC.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>[CH3:11][O:10][CH2:9][C:8]([C:4]1[CH:3]=[C:2]([C:19]#[C:18][Si:15]([CH3:17])([CH3:16])[CH3:14])[CH:7]=[CH:6][CH:5]=1)([CH3:13])[CH3:12]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 67191411HCID 67191411, compound

Product 1

HCID 67187907HCID 67187907, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 21895542Acetonitrile triethylamineSolvent

Procedure

To a solution of 1-bromo-3-(2-methoxy-1,1-dimethyl-ethyl)-benzene (1.62 g, 6.69 mmol) and trimethylsilylacetylene (1.2 mL, 8.7 mmol, 1.3 eq.) in MeCN-Et3N (50 mL, 7:3) was added Pd(PPh3)2Cl2 (0.23 g, 0.33 mmol. 0.05 eq.), CuI (0.038 g, 0.2 mmol, 0.03 eq.) and the mixture refluxed for 16 h. After cooling to ambient temperature and concentration under reduced pressure the residue was chromatographed (EtOAc-hexane, 2:98) to obtain 1.54 g (89%) of the desired product. NMR (DMSO-d6): 7.28-7.00 (m, 4H), 3.16 (s, 2H), 2.98 (s, 3H), 1.00 (s, 6H), 0.1 (s, 9H). MS (DCI): 261 (M+1).

Workup

  1. temperaturethe mixture refluxed for 16 h
  2. concentrationconcentration under reduced pressure the residue
  3. customwas chromatographed (EtOAc-hexane, 2:98)

Sources & evidence

ORD record
ord-f839eab642924d65bb327e751c2414f3
Source dataset
uspto-grants-2013_07
Patent number
US08487116B2

Reaction notes

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