Triethylamine → 2-[(Trimethylsilyl)ethynyl]benzaldehyde

HRID 1644713

반응식

HRID 1644713 반응식
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:10][Si:11]([C:14]#[CH:15])([CH3:13])[CH3:12].C(N(CC)CC)C.C(OCC)(=O)C>O1CCCC1.CCCCCC.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>[CH3:10][Si:11]([CH3:13])([CH3:12])[C:14]#[C:15][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

참가 물질

9

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 811292-Bromobenzaldehyde

생성물 1

HCID 27716412-[(Trimethylsilyl)ethynyl]benzaldehyde수율 82.3%

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

A solution of 2-bromo-benzaldehyde (20.0 g, 108.1 mmol) in anhydrous tetrahydrofuran (200 mL) was degassed with argon for 30 minutes at room temperature. To the above solution was added bis(triphenylphosphine)palladium(II) chloride (Pd(PPh3)2Cl2) (3.79 g, 5.4 mmol) and the mixture was degassed again for an additional 15 minutes. To the reaction mixture were added trimethylsilanyl acetylene (33.97 mL, 216.2 mmol), copper(I) iodide (1.0 g, 5.4 mmol) and triethylamine (29.5 mL, 216.2 mmol), and the mixture was stirred for 16 hours at room temperature. Tetrahydrofuran was removed in vacuo. To the residue was added water (100 mL), and the resulting mixture was extracted with ethyl acetate (3×100 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give a black colored crude product. Flash chromatography (silica gel, 100-200 mesh, 2-5% ethyl acetate in hexane) afforded 2-trimethylsilanylethynyl-benzaldehyde (18.0 g, 82%) as a brown colored solid. MS (ESI+) cald. for C12H14OSi [(M+H)+] 202, obsd. 203.

후처리

  1. customthe mixture was degassed again for an additional 15 minutes
  2. customTetrahydrofuran was removed in vacuo
  3. additionTo the residue was added water (100 mL)
  4. extractionthe resulting mixture was extracted with ethyl acetate (3×100 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a black colored crude product

출처 및 근거

ORD 기록
ord-cfadd7432e134fa5a9fa9c271aba0538
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124629B2

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