Triphenylphosphine → HCID 20083244, compound

HRID 1608936Notes

Reaction equation

HRID 1608936 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[C:9](Br)[CH:10]=2)[O:5][C:4](=[O:13])[CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:34][Si:35]([C:38]#[CH:39])([CH3:37])[CH3:36]>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:39]#[C:38][Si:35]([CH3:37])([CH3:36])[CH3:34])[CH:10]=2)[O:5][C:4](=[O:13])[CH2:3]1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 225689232H-1-Benzopyran-2-one, 6-bromo-3,4-dihydro-4,4-dimethyl-

Product 1

HCID 20083244HCID 20083244, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

The procedure used is substantially in accordance with (Journal of Organic Chemistry, Vol. 46, No. 11, (1981) p 2280-81). To a solution of 2.5 g (9.8 mmol) of 4,4-dimethyl-6-bromo-2-oxo-chroman and 0.087 g (0.3317 mmol) of triphenylphosphine in 36 ml of triethylamine under argon was added 1.74 g (2.5 ml, 17.7 mmol) of trimethylsilylacetylene and 0.027 g (0.12 mmol) of palladium(II) acetate. The mixture was refluxed for 20 hours then cooled to room temperature and filtered. The solvent removed in-vacuo and the resulting residue was purified using flash chromatography (SiO2 ; 5% ethyl acetate in hexanes) to give the title compound as a yellow oil.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. filtrationfiltered
  3. customThe solvent removed in-vacuo
  4. customthe resulting residue was purified

Sources & evidence

ORD record
ord-9923afd7229c4cc2a490f1a2e06fbdfe
Source dataset
uspto-grants-1995_03
Patent number
US05399561

Reaction notes

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