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

HRID 1969390Notes

Reaction equation

HRID 1969390 reaction equation
[OH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>C(Cl)Cl>[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[O:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 12184Ethyl GlycolateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 10899396ethyl 2-((tetrahydro-2H-pyran-2-yl)oxy)acetateYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of ethyl 2-hydroxyacetate (2 g, 20 mmol, TCI) and 3,4-dihydro-2H-pyran (3.2 g, 40 mmol, Alfa) in 40 mL of CH2Cl2 was added PPTS (500 mg, 2 mmol, Aldrich) in portions at rt. The mixture was stirred at rt for 4 hours. The reaction mixture was then washed with brine, and the organic layer was separated and the combined organic phases were dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column chromatography (20:1 (v/v) petroleum ether/EtOAc) to give the desired compound as colorless oil (3.01 g, 81%).

Workup

  1. washThe reaction mixture was then washed with brine
  2. customthe organic layer was separated
  3. dry with materialthe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column chromatography (20:1 (v/v) petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-db39671459eb4d4096c89964b79d52d1
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

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