4-Ethynyl-1-[1-(2,2-dimethylpropyloxy)-cyclopropyl]3-methyl-benzene → Ethyl4-[4-[1-(2,2-dimethylpropyloxy)-cyclopropyl]-3-methyl-phenylethynyl]-benzoate

HRID 51736

Reaktionsgleichung

Reaktionsgleichung von HRID 51736
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([O:12][CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:11][CH2:10]2)=[CH:5][C:4]=1C)#[CH:2].[C:19](O)(=O)C1C=CC=CC=1.[CH2:28]([O:30][C:31](=[O:39])[C:32]1[CH:37]=[CH:36][C:35](I)=[CH:34][CH:33]=1)[CH3:29]>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>[CH3:15][C:14]([CH3:17])([CH3:16])[CH2:13][O:12][C:9]1([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[C:2][C:35]3[CH:36]=[CH:37][C:32]([C:31]([O:30][CH2:28][CH3:29])=[O:39])=[CH:33][CH:34]=3)=[CH:4][C:5]=2[CH3:19])[CH2:11][CH2:10]1

Komponenten

6

Edukt 2

HCID 225690224-Ethynyl-1-[1-(2,2-dimethylpropyloxy)-cyclopropyl]3-methyl-benzene2×HCID 69887287Ethyl-4-iodo-benzoate benzoate2×

Produkt 1

HCID 22568999Ethyl4-[4-[1-(2,2-dimethylpropyloxy)-cyclopropyl]-3-methyl-phenylethynyl]-benzoateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Using General Procedure F; 4-ethynyl-1-[1-(2,2-dimethylpropyloxy)-cyclopropyl]-3-methyl-benzene (Intermediate 85, 75.0 mg, 0.31 mmol) and ethyl-4-iodo benzoate (Reagent A, 86.0 mg, 0.31 mmol) in triethylamine (5 mL) was treated with copper(I)iodide (21.0 mg, 0.11 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)-palladium(II) (78 mg, 0.11 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-4% EtOAc-hexanes) afforded 60.0 mg (50%) of the title compound as an orange solid.

Aufarbeitung

  1. customsparged with argon for 5 minutes

Quellen und Nachweise

ORD-Eintrag
ord-fffbcfe78cbb4a9aa503c9434ea82cc5
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713647B2

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