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

HRID 2052578Notes

Reaction equation

HRID 2052578 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[O:5]1[CH:10]=[CH:9][CH2:8][CH2:7][CH2:6]1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[O:4][CH2:1][C:2]#[CH:3]

Participants

5

Reactant 3

HCID 7859Propargyl alcoholHCID 80803,4-dihydro-2H-pyranHCID 10340Sodium Carbonate

Product 1

HCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranYield 95%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

Propargyl alcohol (13.20 g) and dihydropyran (19.81 g) are placed into a 50-ml container, and 0.2 g of anhydrous p-toluenesulfonic acid is added. The mixture is cooled in an ice bath, then stirred at room temperature for 30 minutes and neutralized with anhydrous sodium carbonate. The resulting solids are separated off. Distillation of the remaining liquid in a vacuum gives 31.3 g of propargyl tetrahydropyranyl ether (yield: 95%), b.p. 75° to 80° C./37 mm Hg.

Workup

  1. additionis added
  2. temperatureThe mixture is cooled in an ice bath
  3. customThe resulting solids are separated off
  4. distillationDistillation of the remaining liquid in a vacuum

Sources & evidence

ORD record
ord-241dbcadfc6646149c7014b6a3e1a3fb
Source dataset
uspto-grants-1980_01
Patent number
US04186141

Reaction notes

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