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

HRID 1765850
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HRID 1765850 반응식
[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]
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참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 608316HCID 608316, 화합물2회

생성물 1

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

시약·촉매·용매 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 178418476HCID 178418476, 화합물촉매
HCID 8058Hexane용매

실험 절차

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.

출처 및 근거

ORD 기록
ord-ce1ab120c39d4fa9ae4e9af50206cbce
출처 데이터셋
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07226951B2

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