4-Ethynyl-1-(1-isopropoxycyclopropyl)-3-ethyl-benzene → Ethyl4-[4-(1-isopropoxycyclopropyl)-3-ethyl-phenylethynyl]-benzoate

HRID 51746Notes

Reaction equation

HRID 51746 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([O:12][CH:13]([CH3:15])[CH3:14])[CH2:11][CH2:10]2)=[CH:5][C:4]=1CC)#[CH:2].[C:18](O)(=O)[C:19]1C=CC=CC=1.[CH2:27]([O:29][C:30](=[O:38])[C:31]1[CH:36]=[CH:35][C:34](I)=[CH:33][CH:32]=1)[CH3:28]>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>[CH:13]([O:12][C:9]1([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[C:2][C:34]3[CH:35]=[CH:36][C:31]([C:30]([O:29][CH2:27][CH3:28])=[O:38])=[CH:32][CH:33]=3)=[CH:8][C:7]=2[CH2:18][CH3:19])[CH2:10][CH2:11]1)([CH3:14])[CH3:15]

Participants

6

Reactant 2

HCID 225688704-Ethynyl-1-(1-isopropoxycyclopropyl)-3-ethyl-benzene2×HCID 69887287Ethyl-4-iodo-benzoate benzoate2×

Product 1

HCID 22568979Ethyl4-[4-(1-isopropoxycyclopropyl)-3-ethyl-phenylethynyl]-benzoateYield 71%

Reagents, catalysts & solvents 3

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

Procedure

Using General Procedure F; 4-ethynyl-1-(1-isopropoxycyclopropyl)-3-ethyl-benzene (Intermediate 95, 108.0 mg, 0.47 mmol) and ethyl-4-iodo benzoate (Reagent A, 130.0 mg, 0.47 mmol) in triethylamine (5 mL) was treated with copper(I)iodide (30.0 mg, 0.16 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)-palladium(II) (110 mg, 0.16 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-4% EtOAc-hexanes) afforded 125.0 mg (71%) of the title compound as an oil.

Workup

  1. customsparged with argon for 5 minutes

Sources & evidence

ORD record
ord-6a4d410e28294ce39582e9f700fe0f86
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

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