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Triethylamine → 1-Methylethyl 3-[2-(trimethylsilyl)ethynyl]benzoate

HRID 2377463
Notes
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Reaction equation

HRID 2377463 reaction equation
[CH:1]([O:4][C:5](=[O:13])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8](Br)[CH:7]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:21][Si:22]([C:25]#[CH:26])([CH3:24])[CH3:23].C(OCC)(=O)C>CCCCCC.[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:1]([O:4][C:5](=[O:13])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:26]#[C:25][Si:22]([CH3:24])([CH3:23])[CH3:21])[CH:7]=1)([CH3:3])[CH3:2]
ParticipantsProcedureSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 608316HCID 608316, compound2×

Product 1

HCID 574242591-Methylethyl 3-[2-(trimethylsilyl)ethynyl]benzoateYield 94%

Reagents, catalysts & solvents 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 8058HexaneSolvent

Procedure

Following General Procedure D and using 3-bromo-benzoic acid isopropyl ester (Intermediate 135, 1.25 g, 5.14 mmol), triethyl amine (12 mL), copper(I)iodide (0.078 g, 0.41 mmol), trimethylsilyl acetylene (4 mL, 28.16 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.288 g, 0.41 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 3% ethyl acetate in hexane as the eluent, the title compound (1.25 g, 94%) was obtained as an orange oil.

Sources & evidence

ORD record
ord-7769c223fad247a59ada16ac79fb4ad3
Source dataset
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07468391B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes