Propargyl alcohol → 3-(4-Fluorophenyl)prop-2-yn-1-ol

HRID 1189079ノート

反応式

HRID 1189079 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH2:9]([OH:12])[C:10]#[CH:11]>C(N(CC)CC)C.[Cu](I)I.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>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:11]#[C:10][CH2:9][OH:12])=[CH:4][CH:3]=1

参加物

6

反応物 2

HCID 7859Propargyl alcoholHCID 96054-Fluoroiodobenzene

生成物 1

HCID 27826983-(4-Fluorophenyl)prop-2-yn-1-ol収率 83.3%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒2 回

反応条件

温度
0 °C

実験手順

In a dry flask containing in suspension copper iodide (84 mg, 0.44 mmol) and triethylamine (24.70 mL), was added Pd(PPh3)2Cl2 (310 mg, 0.44 mmol) under N2. A yellow suspension is obtained. The reaction mixture was cooled to 0° C. in an ice-bath before the addition of 1-fluoro-4-iodobenzene (1.95 g, 8.80 mmol). After five minutes at 0° C., a solution of prop-2-yn-1-ol (493 mg, 8.80 mmol) in triethylamine (4 mL) was slowly added under N2 over a period of 15 min. Immediately the color of the reaction turns to black. The mixture was stirred 0° C. for 30 min and then warmed to room temperature for 20h under N2. Triethylamine was concentrated under reduce pressure and the residue was dissolved in DCM. The organic layer was washed with saturated NH4Cl, water, brine, dried (MgSO4) and concentrated. The crude product was purified by flash chromatography (prepacked 25 g silicagel column, DCM 100% as eluent) to afford 1.10 g of 3-(4-fluorophenyl)prop-2-yn-1-ol (Yield: 83%) as a yellow oil.

後処理

  1. customA yellow suspension is obtained
  2. concentrationTriethylamine was concentrated
  3. dissolutionthe residue was dissolved in DCM
  4. washThe organic layer was washed with saturated NH4Cl, water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (prepacked 25 g silicagel column, DCM 100% as eluent)

出典と根拠

ORDレコード
ord-f23ae57c24374476a6f1e776d068119b
出典データセット
uspto-grants-2014_03
特許番号
US08674106B2

反応ノート

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