Triethylamine → [4-(1-Isopropoxycyclopropyl)-3-methyl-phenylethynyl]-trimethylsilane

HRID 51729Notes

Reaction equation

HRID 51729 reaction equation
[CH2:1]([O:8][C:9]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[C:19]C3C=CC(C(OCC)=O)=CC=3)=[CH:14][C:13]=2[CH3:31])[CH2:11][CH2:10]1)[C:2]1C=CC=CC=1.[CH3:32][Si:33](C#C)([CH3:35])[CH3:34].[CH2:38](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>[CH:1]([O:8][C:9]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[C:19][Si:33]([CH3:35])([CH3:34])[CH3:32])=[CH:14][C:13]=2[CH3:31])[CH2:10][CH2:11]1)([CH3:2])[CH3:38]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 22568984Ethyl4-[4-(1-benzyloxycyclopropyl)-3-methyl-phenylethynyl]-benzoate2×

Product 1

HCID 22568967[4-(1-Isopropoxycyclopropyl)-3-methyl-phenylethynyl]-trimethylsilaneYield 91%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
70 °C

Procedure

Using General Procedure D; 4-bromo-1-(1-isopropoxycyclopropyl)-2-methyl-benzene (Intermediate 79, 250.0 mg, 0.95 mmol) in triethylamine (8 mL) was treated with copper(I)iodide (19.0 mg, 0.10 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) (70.0 mg, 0.1 mmol). The resulting reaction mixture was heated to 70° C. for 5 d. The title compound (250.0 mg, 91%) was isolated by chromatography (0-3% EtOAc-hexanes).

Workup

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

Sources & evidence

ORD record
ord-4735eaa9b7af44fc956a37a6d1182cbb
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

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