2-Naphthaleneacetic acid → HCID 18546144, compound

HRID 1267322Notes

Reaction equation

HRID 1267322 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C[Si](C)(C)O[Si](C)(C)C.[NH2:24][C:25]1[CH:26]=[C:27]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:28]=[CH:29][C:30]=1[OH:31].[CH:39]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:42]=[CH:41][C:40]=1[CH2:49][C:50](O)=O>O.ClC1C=CC=CC=1Cl>[CH:39]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:42]=[CH:41][C:40]=1[CH2:49][C:50]1[O:31][C:30]2[CH:29]=[CH:28][C:27]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:26][C:25]=2[N:24]=1

Participants

7

Reactant 4

HCID 113932-Naphthaleneacetic acidHCID 14812Phosphorus oxide (P4O10)HCID 24764HexamethyldisiloxaneHCID 14368759HCID 14368759, compound

Product 1

HCID 18546144HCID 18546144, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 72391,2-DichlorobenzeneSolvent

Procedure

A mixture of phosphorus pentoxide (P2O5) (12.9 g), hexamethyldisiloxane (29.5 g) and 1,2-dichlorobenzene was heated for 10 minutes under reflux. To the mixture were added ethyl 3-(3-amino-4-hydroxyphenyl)propionate (4.75 g) and 2-naphthylacetic acid (4.23 g). The mixture was heated for 3 hours under reflux. The reaction mixture was poured into water and allowed to extraction with ethyl acetate. The ethyl acetatae layer was washed with water and dried over magnesium sulfate. The solvent was distilled off, and the residue was subjected to silica gel column chromatography. From the fractions eluted with ethyl acetate-hexane (1:4, v/v), ethyl 3-[2-(2-naphthylmethyl)benzoxazol-5-yl]propionate (5.95 g, 73%) was obtained. Recrystallization from ether-isopropyl ether gave colorless needles. Melting point: 81-82° C.

Workup

  1. temperaturewas heated for 10 minutes
  2. temperatureunder reflux
  3. temperatureThe mixture was heated for 3 hours
  4. temperatureunder reflux
  5. extractionallowed to extraction with ethyl acetate
  6. washThe ethyl acetatae layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off
  9. washFrom the fractions eluted with ethyl acetate-hexane (1:4, v/v)

Sources & evidence

ORD record
ord-4483703cce4841fa8ae7a65294017040
Source dataset
uspto-grants-2003_04
Patent number
US06552058B1

Reaction notes

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