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

HRID 2261080

반응식

HRID 2261080 반응식
[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

참가 물질

4

반응물 1

HCID 23349Propargyl ether

생성물 1

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

시약·촉매·용매 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)촉매HCID 702Ethanol용매

반응 조건

온도
70 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-69feb90868a14fc5917c6a2aa2b6f358
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07846925B2

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