Iodine → Ethyl tetrahydro-4-hydroxy-2H-pyran-4-acetate

HRID 735748Notes

Reaction equation

HRID 735748 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.II.Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].S(=O)(=O)(O)O>O1CCCC1.[Zn]>[OH:7][C:4]1([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 7748Ethyl bromoacetateHCID 121599Tetrahydro-4H-pyran-4-one

Product 1

HCID 21936035Ethyl tetrahydro-4-hydroxy-2H-pyran-4-acetateYield 69.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tetrahydro-4H-pyran-4-one (5.5 g, 51.6 mmol), a zinc powder (4.05 g, 61.9 mmol) and a small amount of iodine in tetrahydrofuran (60 ml) was added dropwise ethyl bromoacetate (6.28 ml, 56.7 mmol) under a nitrogen atmosphere. After heating under reflux for 6 hrs., 10% sulfuric acid (50 ml) was carefully added under ice-cooling and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous MgSO4 and concentrated under reduced pressure to give the title compound (6.73 g, 69%) as a colorless oil.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 6 hrs
  3. temperaturecooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ccb328de8a8c4417bd2588f7bb8262d5
Source dataset
uspto-grants-2009_09
Patent number
US07592453B2

Reaction notes

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