Propargyl ether → (1,3-Dihydro-2-benzofuran-5-yl)methanol

HRID 2261080ノート

反応式

HRID 2261080 の反応式
[CH2:1]([O:4][CH2:5][C:6]#[CH:7])[C:2]#[CH:3]>C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[CH2:1]1[C:2]2[C:6](=[CH:7][C:2]([CH2:1][OH:4])=[CH:3][CH:3]=2)[CH2:5][O:4]1

参加物

4

反応物 1

HCID 23349Propargyl ether

生成物 1

HCID 19809558(1,3-Dihydro-2-benzofuran-5-yl)methanol収率 115.3%

試薬・触媒・溶媒 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)触媒HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

In a round bottom flask with reflux condenser were placed 1.0 g of 3-Prop-2-ynyloxy-propyne and 2.08 g of propargylic alcohol in 10 ml ethanol, followed by the addition of 9.8 mg of tris(triphenylphosphine)rhodium chloride (Wilkinson catalyst) at room temperature. The reaction was heated up to 70° C., while the reaction colour turned yellow rapidly. After 1 day stirring at r.t., TLC analysis showed complete conversion of the starting material. The solvent was evaporated, diluted with DCM and extracted with H2O, dried over MgSO4. The brown mixture was purified by flash chromatography using 8/2 cyclohexane/AcOEt as mobile phase affording (1,3-Dihydro-isobenzofuran-5-yl)-methanol as a colourless pure solid (0.92 g, 60%).

後処理

  1. temperatureIn a round bottom flask with reflux condenser
  2. customThe solvent was evaporated
  3. additiondiluted with DCM
  4. extractionextracted with H2O
  5. dry with materialdried over MgSO4
  6. customThe brown mixture was purified by flash chromatography

出典と根拠

ORDレコード
ord-69feb90868a14fc5917c6a2aa2b6f358
出典データセット
uspto-grants-2010_12
特許番号
US07846925B2

反応ノート

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