Iodide Ion → 5-(4-Methoxyphenyl)pent-4-yn-1-ol

HRID 25100

반응식

HRID 25100 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[I-].[CH2:11]([OH:16])[CH2:12][CH2:13][C:14]#[CH:15]>C(NCC)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]#[C:14][CH2:13][CH2:12][CH2:11][OH:16])=[CH:3][CH:4]=1

참가 물질

7

반응물 3

HCID 30165Iodide IonHCID 696764-IodoanisoleHCID 793464-Pentyn-1-ol

생성물 1

HCID 115501385-(4-Methoxyphenyl)pent-4-yn-1-ol수율 88.9%

시약·촉매·용매 3

HCID 11776Triphenylphosphine촉매HCID 24290Palladium Chloride촉매HCID 8021Diethylamine용매

실험 절차

4-Iodoanisol (10 g, 42 mmol), palladium (II) chloride (0.2 g, 1.1 mmol) and triphenylphosphine (0.6 g, 2.2 mmol) were dissolved in diethylamine (100 mL) then cupper(I) iodide (0.5 g, 2.2 mmol) and 4-pentyn-1-ol (5 mL, 53 mmol) were added. The reaction mixture was stirred overnight at room temperature, then the solvent was removed under reduced pressure. Ethyl acetate (150 mL) was added to the residue and the mixture was washed with 2N HCl, brine and water. The organic fraction was isolated, dried with sodium sulfate and the solvent was removed under reduced pressure. The product 16 (7.1 g. 87%) was isolated by flash chromatography (silica gel, 1:2 ethyl acetate/hexanes) as an oily yellow solid. 1H NMR (300 MHz, CDCl3) δ1.88 (m, 2H), 2.53 (m, 2H), 3.72 (s, 3H), 3.74 (m, 2H), 6.83 (d, 2H), 7.45 (d, 2H).

후처리

  1. customthe solvent was removed under reduced pressure
  2. additionEthyl acetate (150 mL) was added to the residue
  3. washthe mixture was washed with 2N HCl, brine and water
  4. customThe organic fraction was isolated
  5. dry with materialdried with sodium sulfate
  6. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-25ced7eb4bce4b60b9dcf3c7dc51c11f
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858614B2

연결된 노트

불러오는 중…