Water → Agn-PC-0MW2M5

HRID 1387314Notes

Reaction equation

HRID 1387314 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

4.3 g(18.9 mmol) of 3-(naphthalen-1-yl)-acrylic acid ethylester prepared in Preparation 6-1) and 3.68 g(18.9 mmol) of tosylmethylisocyanide were dissolved in 100 ml of tetrahydrofuran. 2.55 g(22.7 mmol) of potassium t-butoxide dissolved in 100 ml of tetrahydrofuran was slowly added thereto and the mixture was refluxed for 30 minutes. 100 ml of water was added to the reaction solution to stop the reaction and the solvent was removed under reduced pressure. The reaction solution was extracted with diethylether, washed with aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was removed under reduced pressure and the resulting 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. additionwas slowly added
  2. temperaturethe mixture was refluxed for 30 minutes
  3. customthe reaction
  4. customthe solvent was removed under reduced pressure
  5. extractionThe reaction solution was extracted with diethylether
  6. washwashed with aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5bc7d8f8c304408aa97171134909e358
Source dataset
uspto-grants-2001_07
Patent number
US06268363B1

Reaction notes

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