3,4-dihydro-2H-pyran → Tetrahydropyranyl ether

HRID 615210Notes

Reaction equation

HRID 615210 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[C:7](=[O:10])(O)[O-:8].[Na+]>C(Cl)Cl.CCOCC>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:8][CH:7]1[CH2:5][CH2:4][CH2:3][CH2:2][O:10]1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium Bicarbonate

Product 1

HCID 263182Tetrahydropyranyl ether

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.15 g of the ketone, 1.2 ml of dihydropyran and 10 mg of p-toluolsulfonic acid in 40 ml of methylene chloride is stirred for 30 minutes at 0° C. The product is then diluted with ether, shaken with dilute sodium bicarbonate solution, washed with neutral water, dried via magnesium sulfate and concentrated by evaporation in a vacuum. 1.65 g of the bis-tetrahydropyranyl ether is obtained, which is used without any further purification.

Workup

  1. washwashed with neutral water
  2. dry with materialdried via magnesium sulfate
  3. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-efb6421fc02240e399b98eda2bb56bd0
Source dataset
uspto-grants-1985_02
Patent number
US04497830

Reaction notes

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