3,4-dihydro-2H-pyran → ethyl 2-((tetrahydro-2H-pyran-2-yl)oxy)acetate

HRID 1729980Notes

Reaction equation

HRID 1729980 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH2:2][OH:3].[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[O:3][CH2:2][C:1]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 12184Ethyl GlycolateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 10899396ethyl 2-((tetrahydro-2H-pyran-2-yl)oxy)acetateYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 15.5 g. (0.15 mol.) of ethyl glycolate in 60 ml. of methylene chloride, cooled to 5° C., was added 12.6 g. (0.15 mol.) of dihydropyran, followed by 50 mg. of 4-toluenesulfonic acid monohydrate. After the immediate exothermic reaction which ensued had subsided, the methylene chloride solution was washed successively with water, 5% sodium bicarbonate and water. The dried solution was then evaporated to give 23.8 g. (85% yield) of ethyl 2-(2-tetrahydropyranyloxy)acetate as a clear oil.

Workup

  1. additionwas added 12.6 g
  2. customAfter the immediate exothermic reaction which
  3. washthe methylene chloride solution was washed successively with water, 5% sodium bicarbonate and water
  4. customThe dried solution was then evaporated
  5. customto give 23.8 g

Sources & evidence

ORD record
ord-fa5beee46d0c442d9d20057f8cced7d7
Source dataset
uspto-grants-1976_11
Patent number
US03991053

Reaction notes

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