1-Naphthaldehyde → Methyl (2-(1-naphthyl)-6-benzoxazolyl)acetate

HRID 1372750Notes

Reaction equation

HRID 1372750 reaction equation
[C:1]1([CH:11]=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][C:15]=1O.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>CCO>[C:1]1([C:11]2[O:12][C:15]3[CH:16]=[C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:18]=[CH:19][C:14]=3[N:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 61951-NaphthaldehydeHCID 12217721Iodo benzene diacetateHCID 17858854Methyl 2-(4-amino-3-hydroxyphenyl)acetate

Product 1

HCID 58778440Methyl (2-(1-naphthyl)-6-benzoxazolyl)acetateYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In EtOH (8 ml), 1-naphthaldehyde (263 mg, 1.68 mmol) and methyl 4-amino-3-hydroxyphenylacetate (305 mg, 1.68 mmol) were stirred at room temperature for 12 hours. Iodobenzene diacetate (651 mg, 2.02 mmol) was added to the reaction mixture, followed by stirring at room temperature for 5 minutes. After removal of the solvent by distilling the reaction mixture under reduced pressure, the residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (6:1, v/v) eluate fractions, methyl (2-(1-naphthyl)-6-benzoxazolyl)acetate (223 mg, 42%) was obtained as a pale yellow solid.

Workup

  1. customAfter removal of the solvent
  2. distillationby distilling the reaction mixture under reduced pressure
  3. customthe residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (6:1

Sources & evidence

ORD record
ord-90e088c89fe94f72af7c19ed60ce651e
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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