Ethyl Acetate → Benzyl4-[[(5,5-dimethyl-5,6,7,8-tetrahydro-8-oxo-naphthalen-2-yl)carbonyl]oxy]-benzoate

HRID 2085869Notes

Reaction equation

HRID 2085869 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:11][CH2:10][C:9](=[O:12])[C:8]2[CH:7]=[C:6]([C:13]([OH:15])=[O:14])[CH:5]=[CH:4][C:3]1=2.CN([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22]N=1)C.[C:26]([O:29][CH2:30][CH3:31])(=[O:28])[CH3:27]>CN(C)C=O>[CH2:30]([O:29][C:26](=[O:28])[C:27]1[CH:10]=[CH:11][C:2]([O:14][C:13]([C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH3:16])([CH3:1])[CH2:11][CH2:10][C:9](=[O:12])[C:8]=3[CH:7]=2)=[O:15])=[CH:3][CH:8]=1)[C:31]1[CH:20]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 218852-DimethylaminopyridineHCID 154628445,5-Dimethyl-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid2×

Product 1

HCID 22641986Benzyl4-[[(5,5-dimethyl-5,6,7,8-tetrahydro-8-oxo-naphthalen-2-yl)carbonyl]oxy]-benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5,5-dimethyl-5,6,7,8-tetrahydro-8-oxo-naphthalen-2-carboxylic acid (Compound E3, 386 mg, 1.77 mmol) in dimethylformamide (4 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarboimide hydrochlorde (440 mg, 2.3 mmol) followed by dimethylamino pyridine (DMAP) (280 mg, 2.3 mmol). The mixture was stirred for 10 minutes, and benzyl 4-hydroxy benzoate (426 mg, 1.9 mmol) was added and stirred at ambient temperature for 16 hours. The mixture was diluted with ethyl acetate (100 mL) and washed with water (10 mL), brine (10 mL), dried and solvent distilled off. The title compound was obtained as a pale yellow solid after chromatographic purification.

Workup

  1. stirringstirred at ambient temperature for 16 hours
  2. washwashed with water (10 mL), brine (10 mL)
  3. customdried
  4. distillationsolvent distilled off

Sources & evidence

ORD record
ord-54f77183c9cc45cca8d2439d9462ac8b
Source dataset
uspto-grants-2004_04
Patent number
US06720425B2

Reaction notes

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