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

HRID 2261080Notes

Reaction equation

HRID 2261080 reaction equation
[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

Participants

4

Reactant 1

HCID 23349Propargyl ether

Product 1

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

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-69feb90868a14fc5917c6a2aa2b6f358
Source dataset
uspto-grants-2010_12
Patent number
US07846925B2

Reaction notes

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