Water → HCID 57809191, compound

HRID 2105853Notes

Reaction equation

HRID 2105853 reaction equation
[CH2:1]([O:3][C:4]1[CH:14]=[C:13](I)[CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18].O>C(N(CC)CC)C.CN(C)C=O.[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>[CH2:1]([O:3][C:4]1[CH:14]=[C:13]([C:21]#[C:20][Si:17]([CH3:19])([CH3:18])[CH3:16])[CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

8

Reactant 3

HCID 962WaterHCID 66111TrimethylsilylacetyleneHCID 29934691Ethyl 2-ethoxy-4-iodobenzoate

Product 1

HCID 57809191HCID 57809191, compoundYield 90.3%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 2-ethoxy-4-iodobenzoate (0.763 g, 2.38 mmol, example 14), copper(I) iodide (0.0227 g, 0.119 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.167 g, 0.238 mmol) and (trimethylsilyl)acetylene (0.404 mL, 2.86 mmol) were dissolved under nitrogen in a flame-dried flask in a mixture of triethylamine (3.5 mL) and dimethylformamide (3.5 mL). The reaction mixture was heated at 50° C. for 2 h and then allowed to cool. Water (100 mL) was added and the mixture was extracted with diethyl ether (3×100 mL). The combined organic phases were washed with water (100 mL), brine (100 mL), dried over Sodium sulfate and evaporated. Purification of the crude residue by flash column chromatography (silica gel, eluting with 10% ethyl acetate in hexanes) gave ethyl 2-ethoxy-4-trimethylsilanylethynyl-benzoate as a yellow oil (0.624 g, 90%).

Workup

  1. temperatureto cool
  2. extractionthe mixture was extracted with diethyl ether (3×100 mL)
  3. washThe combined organic phases were washed with water (100 mL), brine (100 mL)
  4. dry with materialdried over Sodium sulfate
  5. customevaporated
  6. customPurification of the crude residue
  7. washby flash column chromatography (silica gel, eluting with 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8a05d2d77f2146648c40633df93cde0b
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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