Water → HCID 18670800, compound

HRID 1059107Notes

Reaction equation

HRID 1059107 reaction equation
C([O:3][C:4]([C:6]1[C:10]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[C:9]([CH3:21])[NH:8][CH:7]=1)=[O:5])C.C(OC(=O)C=CC1C2C(=CC=CC=2)C=CC=1)C.CC(C)([O-])C.[K+].O>O1CCCC1>[OH:5][C:4]([C:6]1[C:10]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[C:9]([CH3:21])[NH:8][CH:7]=1)=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 18670784HCID 18670784, compoundHCID 23665647Potassium tert-butoxideHCID 53428571Ethyl 3-(naphthalen-1-yl)prop-2-enoate

Product 1

HCID 18670800HCID 18670800, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-ethoxycarbonyl-5-methyl-4-(naphthalen-1-yl)-1H-pyrrole 4.3 g(18.9 mmol) of 3-(naphthalen-1-yl)-acrylic acid ethylester prepared in Preparation 6-1) and 3.95 g(18.9 mmol) of α-methyltosylmethylisocyanide disclosed in A. M. van Leusen, et al., Tetrahedron Letter, 1975, 40, 3487 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, which was then refluxed for 30 minutes. To the reaction solution was added 100 ml of water to stop the reaction and the solvent was removed under reduced pressure. The residue was extracted with diethylether, washed with saturated 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 using a solvent mixture of ethyl acetate/n-hexane(1/3, v/v) as an eluent to give 3.50 g(12.5 mmol, Yield 66%) of the title compound.

Workup

  1. additionwas slowly added
  2. temperaturewhich was then 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 saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. additiona solvent mixture of ethyl acetate/n-hexane(1/3

Sources & evidence

ORD record
ord-0bf3e081ee7f49e493a1ec9fd7b75ab5
Source dataset
uspto-grants-2003_02
Patent number
US06518429B2

Reaction notes

Loading…