Methyl 4-iodobenzoate → Methyl 4-(5-hydroxypentynyl)benzoate

HRID 2098368노트

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HRID 2098368 반응식
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH2:12]([OH:17])[CH2:13][CH2:14][C:15]#[CH:16]>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>[OH:17][CH2:12][CH2:13][CH2:14][C:15]#[C:16][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 69273Methyl 4-iodobenzoateHCID 793464-Pentyn-1-ol

생성물 1

HCID 11974394Methyl 4-(5-hydroxypentynyl)benzoate수율 69%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매

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온도
90 °C

실험 절차

Methyl 4-iodobenzoate (13.1 g, 60 mmol), PdCl2(PPh3)2 (2.0 g, 3 mmol), and CuI (855 mg, 4.5 mmol) were added to TEA (60 mL). The mixture is degassed while stirring by bubbling N2 vigorously into the solution. Pent-4-yn-1-ol (5.5 g, 66 mmol) was added by syringe. The mixture was heated at 90° C. overnight. After cooling, the crude mixture was concentrated by rotary evaporation and pumped on the high vacuum for 1 h. The oil was dissolved in DCM and adsorbed onto Celite followed by purification by chromatography (gradient 10-100% EtOAc/Hexanes) to give the title compound as a light yellow powder (9 g, 69%). 1H NMR (400 MHz, CDCl3) δ 7.95 (dd, 2H, J=9.0, 1.5 Hz), 7.44 (dd, 2H, J=9.0, 1.5 Hz), 3.90 (s, 3H), 3.85 (m, 2H), 2.57 (t, 2H, J=5.5 Hz), 1.87 (m, 2H), 1.42 (t, 1H, J=5.5 Hz); ES/MS calcd. for C13H16O3+ 219.1, found m/z=219 (M+H)+.

후처리

  1. customThe mixture is degassed
  2. customby bubbling N2 vigorously into the solution
  3. temperatureAfter cooling
  4. concentrationthe crude mixture was concentrated by rotary evaporation
  5. dissolutionThe oil was dissolved in DCM
  6. customfollowed by purification by chromatography (gradient 10-100% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-7d35fcf793cd43128768f8e2c2acb7c4
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450490B2

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