5-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one → 5-(Benzyloxy)-2-methyl-4H-pyran-4-one

HRID 1056896Notes

Reaction equation

HRID 1056896 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH:11]=[C:12]([CH2:15]Cl)[O:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[NH4+].[Cl-].[Zn]>[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH:11]=[C:12]([CH3:15])[O:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 37033215-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one

Product 1

HCID 53141715-(Benzyloxy)-2-methyl-4H-pyran-4-oneYield 42%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 5-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one (1 10 g, 0.44 mol) in saturated aqueous NH4Cl (1 L) was added Zn powder (58.5 g, 0.9 mol) at r.t. and the mixture was stirred at 70° C. for 2 h. The mixture was partitioned between water and EtOAc, the EtOAc phase was collected and water phase was extracted with EtOAc twice. The combined EtOAc layer was washed with brine, dried over a2S04, and concentrated. The residue was purified by silica gel chromatography to give 40 g (42%) of 5-(benzyloxy)-2-methyl-4H-pyran-4-one.

Workup

  1. customThe mixture was partitioned between water and EtOAc
  2. customthe EtOAc phase was collected
  3. extractionwater phase was extracted with EtOAc twice
  4. washThe combined EtOAc layer was washed with brine
  5. customdried over a2S04
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0cf80fff50014e45a675eaa746725989
Source dataset
uspto-grants-2016_07
Patent number
US09399651B2

Reaction notes

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