Propargyl alcohol → Tetrahydro-2-(2-propynyloxy)-2H-pyran

HRID 1582514Notes

Reaction equation

HRID 1582514 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([OH:9])[C:7]#[CH:8].[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1>ClCCl>[CH2:6]([O:9][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][O:10]1)[C:7]#[CH:8]

Participants

5

Reactant 3

HCID 7859Propargyl alcoholHCID 80803,4-dihydro-2H-pyranHCID 24813Phosphorus oxychloride

Product 1

HCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of phosphoryl chloride (0.5 ml in 10 ml of dichloromethane [DCM])) was added with care to a solution of prop-2-yn-1-ol (7.00 g, 125 mmol) and dihydropyran (10.50 g, 125 mmol) in DCM (80 ml). The reaction mixture was stirred at room temperature for 16 h, washed with sodium hydrogen carbonate solution (3 times), dried (MgSO4) and the solvent removed in vacuo to yield a colorless oil. The crude product was purified by column chromatography [silica gel, eluted with hexane/ethyl acetate (4:1), Rf: 0.43] to yield a colorless oil.

Workup

  1. washwashed with sodium hydrogen carbonate solution (3 times)
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customto yield a colorless oil
  5. customThe crude product was purified by column chromatography [silica gel, eluted with hexane/ethyl acetate (4:1), Rf: 0.43]
  6. customto yield a colorless oil

Sources & evidence

ORD record
ord-86129c29bf484dc8be09d8b9400aad3c
Source dataset
uspto-grants-2004_05
Patent number
US06737124B2

Reaction notes

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