Potassium Hydroxide → HCID 18766458, compound

HRID 480691Notes

Reaction equation

HRID 480691 reaction equation
C([O:3][C:4]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]([CH:22]=[CH:23][CH:24]=1)[O:11][C:12]([CH3:21])([CH3:20])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:5])C.[OH-].[K+]>C(O)C>[C:16]([O:15][C:13]([C:12]([CH3:21])([O:11][C:10]1[CH:9]=[C:8]([CH2:7][CH2:6][C:4]([OH:5])=[O:3])[CH:24]=[CH:23][CH:22]=1)[CH3:20])=[O:14])([CH3:17])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18766548HCID 18766548, compound

Product 1

HCID 18766458HCID 18766458, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl 2-[3-[2-(ethoxycarbonyl)ethyl]phenoxy]-2-methylpropionate (37.1 g, 0.11 mmol) was dissolved in ethanol. Subsequently, aqueous 10% potassium hydroxide solution was added dropwise, and the mixture was stirred overnight at room temperature. The resultant mixture was concentrated under reduced pressure, and then an aqueous 5% potassium hydrogensulfate solution was added thereto. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine. The mixture was subjected to drying over sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (n-hexane/ethyl acetate=3/2), whereby the target compound was obtained (32.0 g, 94%).

Workup

  1. concentrationThe resultant mixture was concentrated under reduced pressure
  2. additionan aqueous 5% potassium hydrogensulfate solution was added
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialto drying over sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (n-hexane/ethyl acetate=3/2), whereby the target compound
  6. customwas obtained (32.0 g, 94%)

Sources & evidence

ORD record
ord-47c457258bc64b2187b199f9d789f366
Source dataset
uspto-grants-2003_11
Patent number
US06653334B1

Reaction notes

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