Triethylamine → Ethyl 4-((trimethylsilyl)ethynyl)benzoate

HRID 583700Notes

Reaction equation

HRID 583700 reaction equation
[Si:1]([C:5]#[CH:6])([CH3:4])([CH3:3])[CH3:2].Br[C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=1.CCN(CC)CC>CC#N.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>[CH3:2][Si:1]([C:5]#[C:6][C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=1)([CH3:4])[CH3:3]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 22043Ethyl 4-bromobenzoateHCID 66111Trimethylsilylacetylene

Product 1

HCID 10729134Ethyl 4-((trimethylsilyl)ethynyl)benzoate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

TMS-acetylene (Aldrich) (5.0 mL, 35.5 mmol), ethyl 4-bromobenzoate (58 mL, 35.5 mmol) and Et3N (20 mL, 144 mmol) were combined in 50 mL CH3CN in a glass pressure tube. (Ph3P)2PdCl2 (198 mg, 0.28 mmol) and CuI (100 mg, 0.53 mmol) were added, and the reaction was sealed and heated at 100° for 18 h. Dilution with EtOAc, washing twice with water, then brine, drying and concentration provided 29-1 as a brown liquid.

Workup

  1. customthe reaction was sealed
  2. temperatureheated at 100° for 18 h
  3. washDilution with EtOAc, washing twice with water
  4. dry with materialbrine, drying
  5. concentrationconcentration

Sources & evidence

ORD record
ord-8375d13d9c0448dfab1bbdf99883324c
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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