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

HRID 1699336Notes

Reaction equation

HRID 1699336 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.N1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:23]([O:26][CH2:27][CH3:28])(=[O:25])[CH3:24]>CN(C)C=O>[CH2:27]([O:26][C:23](=[O:25])[C:24]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:28]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 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 dimethylaniino 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-0ee9099700fa447b8d2d689790ff4388
Source dataset
uspto-grants-2002_02
Patent number
US06344561B2

Reaction notes

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