Trimethylsilylacetylene → [4-(1-Benzyloxycyclopropyl)phenylethynyl]-trimethylsilane

HRID 1935856Notes

Reaction equation

HRID 1935856 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:19][Si:20]([C:23]#[CH:24])([CH3:22])[CH3:21]>C(N(CC)CC)C.[Cu]I.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>[CH2:12]([O:11][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([C:24]#[C:23][Si:20]([CH3:22])([CH3:21])[CH3:19])=[CH:3][CH:4]=2)[CH2:10][CH2:9]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 225688021-Bromo-4-(1-benzyloxycyclopropyl)benzene2×

Product 1

HCID 22568904[4-(1-Benzyloxycyclopropyl)phenylethynyl]-trimethylsilaneYield 88.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

Using General Procedure D; 1-bromo-4-(1-benzyloxycyclopropyl)-benzene (Intermediate 69, 160.0 mg, 0.53 mmol) in triethylamine (5 mL) was treated with copper(I)iodide (10.0 mg, 0.05 mmol) and then sparged with argon for 5 minutes. Trimethylsilylacetylene (0.70 g, 7.1 mmols) was then added followed by dichlorobis-(triphenylphosphine)palladium(II) (37.0 mg, 0.05 mmol). The resulting reaction mixture was heated to 70° C. for 5 d. The title compound (150.0 mg, 83%) was isolated by chromatography (0-3% EtOAc-hexanes) as a pale-yellow oil.

Workup

  1. customsparged with argon for 5 minutes
  2. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-bfe8abaea8074355ab5fcb41e7e29a0e
Source dataset
uspto-grants-2002_05
Patent number
US06387892B1

Reaction notes

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