Ethyl Salicylate → HCID 70062724, compound

HRID 2293658Notes

Reaction equation

HRID 2293658 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14]([O:23][CH2:24][CH3:25])(=[O:22])[C:15]1[C:16](=[CH:18][CH:19]=[CH:20][CH:21]=1)[OH:17].C(N=C=NC(C)C)(C)C>ClCCl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([C:16]2([OH:17])[CH:18]=[CH:19][CH:20]=[CH:21][CH:15]2[C:14]([O:23][CH2:24][CH3:25])=[O:22])=[O:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8365Ethyl SalicylateHCID 12734DiisopropylcarbodiimideHCID 16757Benzenepentanoic acid

Product 1

HCID 70062724HCID 70062724, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1.07 g of 5-phenylvaleric acid and 60 mg of N,N-dimethylaminopyridine in 20 ml of dichloromethane is added 0.75 ml of ethyl salicylate, followed by 0.95 ml of diisopropyl carbodiimide. After 18 hours, the mixture is concentrated under reduced pressure, and the residue triturated with ether. The organic phase is washed with aq. sodium bicarbonate and brine, dried (magnesium sulfate), and concentrated under reduced pressure. Flash chromatography on silica with 10% ethyl acetate in hexane affords 1.60 g of the title product as a colorless oil.

Workup

  1. concentrationthe mixture is concentrated under reduced pressure
  2. customthe residue triturated with ether
  3. washThe organic phase is washed with aq. sodium bicarbonate and brine
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-380fcda0e92a425bbffb7320d76099ed
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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