Ethanol → HCID 68567766, compound

HRID 1071519Notes

Reaction equation

HRID 1071519 reaction equation
[Na].[CH3:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)COS(C)(=O)=O)[CH2:6]2.O.[CH2:27](O)[CH3:28]>>[CH3:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH:20]=[CH:25][C:24]1[CH:23]=[CH:22][CH:21]=[CH:28][CH:27]=1)[CH2:6]2

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 962WaterHCID 5360545SodiumHCID 20800560HCID 20800560, compound

Product 1

HCID 68567766HCID 68567766, compound

Procedure

Under argon sodium metal (0.58 g, 24.37 mmol) was slowly added to anhydrous ethanol. After all the sodium was reacted methanesulfonic acid 2-(5-methyl-1-oxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-ethyl ester (5.61 g, 16.25 mmol) dissolved in ethanol was added to the reaction mixture and the solution was stirred for 6 h at room temp. The reaction was poured into water and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was used in the next step without further purification. Yield 3.64 g.

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe aqueous layer was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe solution was filtered
  6. customthe solvent removed under reduced pressure
  7. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-4fa65a44f54241bfb89869f9fcbc91fc
Source dataset
uspto-grants-2005_06
Patent number
US06906067B2

Reaction notes

Loading…