3,4-dihydro-2H-pyran → 2-But-3-enoxyoxane

HRID 1582515Notes

Reaction equation

HRID 1582515 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([OH:10])[C:7]#[C:8][CH3:9].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1>C(Cl)Cl>[CH2:6]([O:10][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:11]1)[CH2:7][CH:8]=[CH2:9]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 129912-Butyn-1-olHCID 24813Phosphorus oxychloride

Product 1

HCID 3199452-But-3-enoxyoxane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of phosphoryl chloride (0.5 ml in 10 ml of DCM) was added with care to a solution of but-2-yn-1-ol (8.75 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, euted with hexane/ethyl acetate (4:1), Rf: 0.36] 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, euted with hexane/ethyl acetate (4:1), Rf: 0.36]
  6. customto yield a colorless oil

Sources & evidence

ORD record
ord-1813885332774ff78541c40e688d6bc8
Source dataset
uspto-grants-2004_05
Patent number
US06737124B2

Reaction notes

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