Water → HCID 22600510, compound

HRID 1760089Notes

Reaction equation

HRID 1760089 reaction equation
Br[C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[C:20]([Si:22]([CH3:25])([CH3:24])[CH3:23])#[CH:21].C(NC(C)C)(C)C.O>C1COCC1.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.[Cu]I>[CH3:23][Si:22]([C:20]#[C:21][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1)([CH3:25])[CH3:24]

Participants

8

Reactant 4

HCID 962WaterHCID 7912DiisopropylamineHCID 66111TrimethylsilylacetyleneHCID 15540686Methyl 4-(4-bromobenzoyl)benzoate

Product 1

HCID 22600510HCID 22600510, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of methyl 4-(4-bromobenzoyl)benzoate (1.20 g, 3.76 mmol), ethynyltrimethylsilane (554 mg, 5.66 mmol), (PPh3)2PdCl2(106 mg, 0.151 mmol), CuI (14.3 mg, 0.075 mmol) in THF (30 ml), diisopropyl amine (799 mg, 7.92 mmol) was added dropwise under argon atmosphere. The mixture was stirred at 50° C. for 4 h. Water was added to the mixture after cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=10/1) to give methyl 4-(4-trimethylsilylethynylbenzoyl)benzoate (83%).

Workup

  1. additionwas added dropwise under argon atmosphere
  2. temperatureafter cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-9b51b6242da54bcf99abce1f772edd2e
Source dataset
uspto-grants-2005_01
Patent number
US06838574B1

Reaction notes

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