Potassium Iodide → Ethyl 3-oxo-2-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)benzyl)butanoate

HRID 1617185Notes

Reaction equation

HRID 1617185 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].Cl[CH2:13][C:14]1[CH:27]=[CH:26][C:17]([CH2:18][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[CH:16][CH:15]=1.[I-].[K+]>C1COCC1>[O:4]=[C:3]([CH3:5])[CH:2]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[CH:26][CH:27]=1)[C:1]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8868Ethyl AcetoacetateHCID 24758Sodium hydrideHCID 104902622-(4-(chloromethyl)benzyloxy)tetrahydro-2H-pyran

Product 1

HCID 68414491Ethyl 3-oxo-2-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)benzyl)butanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl acetoacetate (11.7 ml) was added to a stirred suspension of sodium hydride (60% disp. in oil, 3.8 g) in THF (200 ml) at 0° C. under nitrogen. After 1 h, a solution of 2-(4-(chloromethyl)benzyloxy)tetrahydro-2H-pyran (22.2 g) in THF (50 ml) was added, the mixture warmed to rt, then potassium iodide (16 g) added and heated under reflux for 48 h. The mixture was partitioned between water and ether, the organics separated, washed with water, dried and evaporated under reduced pressure. The residue was purified by column chromatography eluting with 20% EtOAc in isohexane to afford the subtitle compound, 15.66 g.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 48 h
  3. customThe mixture was partitioned between water and ether
  4. washthe organics separated, washed with water
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography
  8. washeluting with 20% EtOAc in isohexane

Sources & evidence

ORD record
ord-ff79f9e2d9954695a848b3af94dfc6e0
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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