tert-Butanol → HCID 18948446, compound

HRID 1768587Notes

Reaction equation

HRID 1768587 reaction equation
[OH-].[K+].[C:3]1([CH2:13][CH:14](C(OCC)=O)[C:15](OCC)=[O:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[C:25]([OH:29])([CH3:28])([CH3:27])[CH3:26].C1(N=C=NC2CCCCC2)CCCCC1>CO>[C:3]1([CH2:13][CH2:14][C:15]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 14797Potassium HydroxideHCID 9972002Diethyl (1-naphthyl)methylmalonate

Product 1

HCID 18948446HCID 18948446, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

18.7 g (0.333 mmole) of potassium hydroxide were added to a solution of 20 g (66.6 mmole) of diethyl (1-naphthyl)methylmalonate dissolved in 200 ml of 80% v/v aqueous methanol, The mixture was then stirred at room temperature for 1 hour, after which it was concentrated by evaporation under reduced pressure. The residue was dissolved in water, and the resulting solution was washed with ethyl acetate. The aqueous solution was acidified with concentrated hydrochloric acid and then extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was decarboxylated by heating at 200° C. for 30 minutes, and was then suspended in 200 ml of diethyl ether. 19 ml of t-butanol, 16.5 g (80 mmole) of dicyclohexylcarbodiimide and 0.8 g of N,N-dimethylaminopyridine were added to the suspension. The mixture was allowed to stand for 24 hours. The precipitated insoluble materials were removed by filtration, and the filtrate was concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel (eluent: methylene chloride), to afford 12.18 g (71.4%) of the title compound as a pale yellow oil.

Workup

  1. concentrationafter which it was concentrated by evaporation under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. washthe resulting solution was washed with ethyl acetate
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. temperatureby heating at 200° C. for 30 minutes
  8. waitto stand for 24 hours
  9. customThe precipitated insoluble materials were removed by filtration
  10. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  11. customThe residue was purified by column chromatography through silica gel (eluent: methylene chloride)

Sources & evidence

ORD record
ord-b21868d55c83482eb1e46b34b9eaba83
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

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