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

HRID 2387839
Notes
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Reaction equation

HRID 2387839 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8028
Tetrahydrofuran
Solvent
2×

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-56ba53265f7e4da887688d41a174072e
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08268990B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes