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

HRID 1517871Notes

Reaction equation

HRID 1517871 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, Aldrich) and 3,4-dihydro-2H-pyran (3.2 g, 40 mmol, Alfa) in 40 mL of CH2Cl2 was added PPTS (500 mg, 2 mmol) slowly at rt. The mixture was stirred at rt for 4 hours, and then the mixture was washed with brine (20 mL×2), the combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE: EtOAc=20:1) to give colorless oil (3.01 g, 81%).

Workup

  1. washthe mixture was washed with brine (20 mL×2)
  2. dry with materialthe combined organic phases were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (PE: EtOAc=20:1)

Sources & evidence

ORD record
ord-c2abeba254e7414a9b2313cc3f8991fe
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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