Triethylamine → 3-((Trimethylsilyl)ethynyl)phenol

HRID 1917006노트

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HRID 1917006 반응식
CCN(CC)CC.I[C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1.[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18].CCCCCC.CC(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>[CH3:16][Si:17]([CH3:19])([CH3:18])[C:20]#[C:21][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 122723-IodophenolHCID 66111TrimethylsilylacetyleneHCID 21880519Acetone hexane

생성물 1

HCID 220877193-((Trimethylsilyl)ethynyl)phenol수율 100%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a stirred solution of PdCl2(PPh3)2 (46 mg, 0.04 mmol), CuI (15 mg, 0.08 mmol), and Et3N (0.303 g, 0.42 mL, 3 mmol) in 10 mL of THF under nitrogen was added 3-iodophenol (0.440 g, 2 mmol) by syringe. The reaction mixture was cooled to 0° C., and trimethylsilylacetylene (0.206 g, 0.30 mL, 2.1 mmol) was added dropwise over 30 min. The reaction mixture was stirred at room temperature overnight and was filtered through Celite to remove Pd and Cu catalysts. Column chromatography (n-hexane/Acetone 6:1) yielded 3-(2-(trimethylsilyl)ethynyl)phenol (380 mg, 2.0 mmol, >99%) as a light brown oil. This compound was diluted with THF (6 mL) and MeOH (6 mL), and 10% aqueous KOH (6 mL) was added. After stirring for 2 hr, the reaction mixture was neutralized by 1 N HCl and evaporated, extracted with CH2Cl2, and dried (Na2SO4). Column chromatography (n-hexane/acetone 5:1) yielded 3-ethynylphenol (162.8 mg, 70%) as a yellow oil.

후처리

  1. filtrationwas filtered through Celite
  2. customto remove Pd and Cu catalysts

출처 및 근거

ORD 기록
ord-2f0c787ebf264b77b35d29c4c134180e
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618162B2

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