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

HRID 25100

反応式

HRID 25100 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11776Triphenylphosphine触媒HCID 24290Palladium Chloride触媒HCID 8021Diethylamine溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-25ced7eb4bce4b60b9dcf3c7dc51c11f
出典データセット
uspto-grants-2005_02
特許番号
US06858614B2

関連ノート

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