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

HRID 1765850
Notes
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Reaction equation

HRID 1765850 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-ce1ab120c39d4fa9ae4e9af50206cbce
Source dataset
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07226951B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes