Water → Agn-PC-0MW2M5

HRID 1059111Notes

Reaction equation

HRID 1059111 reaction equation
[C:1]1([CH:11]=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.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>[CH2:16]([O:15][C:13]([C:12]1[C:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)=[CH:30][NH:29][CH:28]=1)=[O:14])[CH3:17]

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

500 mg(1.89 mmol) of ethyl 3-(naphthalen-1-yl)acrylate prepared in Example 80-1) and 368 mg(1.89 mmol) of tosylmethylisocyanide were dissolved in 10 ml of tetrahydrofuran. 255 mg(2.27 mmol) of potassium t-butoxide dissolved in tetrahydrofuran(10 ml) was slowly added thereto and the mixture was refluxed for 30 minutes. 10 ml of water was added to the reaction solution to stop the reaction and the solvent was removed under reduced pressure. The residue was extracted with diethylether, washed with aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was subjected to column chromatography(eluent: ethyl acetate/hexane=1/3, v/v) to give 385 mg(1.45 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 residue was extracted with diethylether
  6. washwashed with aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9a6e708267684e5ea796b20f89fe71ae
Source dataset
uspto-grants-2003_02
Patent number
US06518429B2

Reaction notes

Loading…