Water → Agn-PC-0MW2M5

HRID 2304577Notes

Reaction equation

HRID 2304577 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]=[CH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)[CH3:2].S([CH2:28][N+:29]#[C-:30])(C1C=CC(C)=CC=1)(=O)=O.CC(C)([O-])C.[K+].O>O1CCCC1.C(OCC)(=O)C.CCCCCC>[CH2:1]([O:3][C:4]([C:5]1[C:6]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][CH:8]=2)=[CH:30][NH:29][CH:28]=1)=[O:17])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxideHCID 53428571Ethyl 3-(naphthalen-1-yl)prop-2-enoate

Product 1

HCID 9943237Agn-PC-0MW2M5Yield 77%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

5 g(18.9 mmol) of 3-(naphthalen-1-yl)-acrylic acid ethyl ester prepared in Preparation 2-1) and 3.68 g(18.9 mmol) of tosylmethylisocyanide were dissolved in 100 ml of tetrahydrofuran. To this solution was slowly added 2.55 g(22.7 mmol) of potassium t-butoxide dissolved in 100 ml of tetrahydrofuran, then the resulting solution was refluxed for 30 minutes. 100 ml of water was added to the reaction solution in order to stop the reaction, and the solvent was eliminated under reduced pressure. The residue was extracted with diethylether, washed with aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was subjected to silica gel column chromatography(eluent: ethyl acetate/n-hexane=1/3, v/v) to obtain 3.85 g(14.5 mmol, Yield 77%) of the title compound.

Workup

  1. temperaturethe resulting solution was refluxed for 30 minutes
  2. customthe reaction
  3. extractionThe residue was extracted with diethylether
  4. washwashed with aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1eb38a2b2f9b4320bf72f7829fda27b1
Source dataset
uspto-grants-2002_08
Patent number
US06436960B1

Reaction notes

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