Trimethylsilylacetylene → HCID 131722720, compound

HRID 844794Notes

Reaction equation

HRID 844794 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:21])([CH3:20])[O:14][SiH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[C:9]([CH:22]([CH3:24])[CH3:23])[CH:8]=1)(=O)=O.[CH3:27][Si:28]([C:31]#[CH:32])([CH3:30])[CH3:29]>C(N(CC)CC)C.CN(C=O)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>[C:16]([SiH2:15][O:14][C:13]([CH3:21])([CH3:20])[C:10]1[CH:11]=[CH:12][C:7]([C:32]#[C:31][Si:28]([CH3:30])([CH3:29])[CH3:27])=[CH:8][C:9]=1[CH:22]([CH3:24])[CH3:23])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 131722721HCID 131722721, compound2×

Product 1

HCID 131722720HCID 131722720, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 4-(tert-butyl-dimethyl-silanyloxymethyl)-3-isopropyl-phenyl 1,1,1-trifluoro-methanesulfonate (Intermediate 150, 970.0 mg, 2.35 mmols) in triethylamine (2 mL) and 6 mL DMF was sparged with argon for 15 minutes. Trimethylsilyl acetylene (1.00 g, 10.6 mmols) was then added followed by dichlorobis(triphenylphosphine)palladium(II) (66.0 mg, 0.09 mmol). The resulting reaction mixture was heated to 95° C. for 20 hours. The solution was cooled to room temperature and concentrated under reduced pressure. The title compound (200.0 mg, 78%) was isolated by chromatography (0-25% EtOAc-hexanes) as an orange oil.

Workup

  1. customThe resulting reaction mixture
  2. temperatureThe solution was cooled to room temperature
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-23949205c769463889fba3d290db18ce
Source dataset
uspto-grants-2002_04
Patent number
US06380256B1

Reaction notes

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