Benzyl 2-hydroxy-2-(tetrahydro-2H-pyran-4-yl)acetate → Benzyl 2-oxo-2-(tetrahydro-2H-pyran-4-yl)acetate

HRID 516887Notes

Reaction equation

HRID 516887 reaction equation
[OH:1][CH:2]([CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4]>ClCCl>[O:1]=[C:2]([CH:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4]

Participants

3

Reactant 1

HCID 90185045Benzyl 2-hydroxy-2-(tetrahydro-2H-pyran-4-yl)acetate

Product 1

HCID 90184979Benzyl 2-oxo-2-(tetrahydro-2H-pyran-4-yl)acetateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A Dess-Martinn reagent (5.7 g, 13.44 mmol) was added to a solution of benzyl 2-hydroxy-2-(tetrahydro-2H-pyran-4-yl)acetate (2.1 g, 8.404 mmol) in dichloromethane (50 ml) at room temperature, and the mixture was stirred for 15 hr. The reaction mixture was quenched with 10% sodium thiosulfate and was extracted with dichloromethane. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine and was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate=9:1) to give the title compound as a light yellow oil (1.8 g, yield 90%).

Workup

  1. customThe reaction mixture was quenched with 10% sodium thiosulfate
  2. extractionwas extracted with dichloromethane
  3. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe residue was chromatographed on silica gel column (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-0f5f6ed958ac4c1c963522207fc6ebc9
Source dataset
uspto-grants-2015_08
Patent number
US09115079B2

Reaction notes

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