Benzyl Bromide → Diethyl 1-(ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylate

HRID 913172Notes

Reaction equation

HRID 913172 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([OH:22])=[C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:13]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:9]([O:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([O:22][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:13]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH3:10]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 58012479Diethyl 1-(ethyloxy)-4-hydroxy-2,3-naphthalenedicarboxylate

Product 1

HCID 58012512Diethyl 1-(ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzyl bromide (1.32 ml, 11.1 mmol) was added to a stirred solution of diethyl 1-(ethyloxy)-4-hydroxy-2,3-naphthalenedicarboxylate (2.45 g, 7.38 mmol) and potassium carbonate (1.53 g, 11.1 mmol) in acetone (50 ml). The reaction mixture was refluxed for 1 hour under an atmosphere of argon. The resulting mixture was evaporated and the residue was partitioned between 2× ethylacetate and brine. The combined organics were washed with water and dried over magnesium sulphate. The clear oil was purified by chromatography on silica gel, eluting with ethyl acetate (0-40%) in hexane to give the title compound as clear oil (3.05 g, 7.23 mmol). LC/MS: Rt=3.77, [MH]+ 423

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour under an atmosphere of argon
  2. customThe resulting mixture was evaporated
  3. customthe residue was partitioned between 2× ethylacetate and brine
  4. washThe combined organics were washed with water
  5. dry with materialdried over magnesium sulphate
  6. customThe clear oil was purified by chromatography on silica gel
  7. washeluting with ethyl acetate (0-40%) in hexane

Sources & evidence

ORD record
ord-544897942775406e889de547b19c579b
Source dataset
uspto-grants-2011_09
Patent number
US08026270B2

Reaction notes

Loading…