Cyclopropylacetylene → HCID 57804112, compound

HRID 2102902Notes

Reaction equation

HRID 2102902 reaction equation
Br[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:13][CH2:14][CH:15]1[CH2:17][CH2:16]1.[C:18]([CH:20]1[CH2:22][CH2:21]1)#[CH:19]>C1(C)C=CC=CC=1.C(N(CC)CC)C.CO.[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:20]1([C:18]#[C:19][C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=2[O:13][CH2:14][CH:15]2[CH2:17][CH2:16]2)[CH2:22][CH2:21]1

Participants

8

Reactant 2

HCID 138823CyclopropylacetyleneHCID 57804164HCID 57804164, compound

Product 1

HCID 57804112HCID 57804112, compoundYield 61%

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

Ethyl 4-bromo-3-(cyclopropylmethoxy)benzoate (0.77 g, 2.57 mmol), ethynylcyclopropane (0.45 mL of a 70% w/v solution in toluene, 3.86 mmol), copper(I) iodide (49 mg, 0.26 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.36 g, 0.51 mmol) were placed in 50 mL triethylamine and stirred in a sealed tube at room temperature for 20 h. The reaction was diluted with MeOH and filtered through Celite®., then the filtrate was concentrated to an oil. Purification by column chromatography on silica gel using 25% EtOAc/hexane gave the product (0.47 g, 61%) as a brown oil.

Workup

  1. filtrationfiltered through Celite®
  2. concentration, then the filtrate was concentrated to an oil
  3. customPurification by column chromatography on silica gel using 25% EtOAc/hexane

Sources & evidence

ORD record
ord-77f1f828eb92436b9b1d44ead980cd40
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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