4-(Methylthio)benzaldehyde → HCID 69055255, compound

HRID 2196611Notes

Reaction equation

HRID 2196611 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8]C)=O.[CH3:10][S:11][C:12]1[CH:19]=[CH:18][C:15](C=O)=[CH:14][CH:13]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:10][S:11][C:12]1[CH:19]=[CH:18][C:15]([N:2]2[CH2:3][CH2:4][CH2:5][C:6]2=[O:8])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 769854-(Methylthio)benzaldehydeHCID 516892Sodium BicarbonateHCID 27563834-Aminobutyric acid methyl ester hydrochlorideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 69055255HCID 69055255, compoundYield 105.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

3 g of methyl 4-aminobutyrate hydrochloride and 2.8 ml of triethylamine were added to a chloroform solution of 2 g of 4-(methylthio)benzaldehyde, and 8.4 g of sodium triacetoxyborohydride was added to it, and stirred overnight. Aqueous sodium hydrogencarbonate solution was added to it, extracted with chloroform, and the organic layer was washed with saturated saline water. This was dried with anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography to obtain 2.88 g of 1-[4-(methylthio)phenyl]pyrrolidin-2-one as a colorless oil.

Workup

  1. additionwas added to it
  2. extractionextracted with chloroform
  3. washthe organic layer was washed with saturated saline water
  4. dry with materialThis was dried with anhydrous sodium sulfate
  5. customthe solvent was evaporated away under reduced pressure
  6. customthe resulting residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-195a127fe3a8465e9791bd550e2149b1
Source dataset
uspto-grants-2012_12
Patent number
US08338460B2

Reaction notes

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